Abstract
Background: 1,4-Diazepines are two nitrogen containing seven membered heterocyclic compounds and associated with a wide range of biological activities. Due to its medicinal importance, scientists are actively involved in the synthesis, reactions and biological evaluation of 1,4-diazepines since number of decades.
Objective: The primary purpose of this review is to discuss the synthetic schemes and reactivity of 1,4- diazepines. This article also describes biological aspects of 1,4-diazepine derivatives, that can be usefully exploited for the pharmaceutical sector.
Conclusion: This review summarizes the abundant literature on synthetic routes, chemical reactions and biological attributes of 1,4-diazepine derivatives. We concluded that 1,4-diazepines have significant importance due to their biological activities like antipsychotic, anxiolytic, anthelmintic, anticonvulsant, antibacterial, antifungal and anticancer. 1,4-diazepine derivatives with significant biological activities could be explored for potential use in the pharmaceutical industries.
Keywords: 1, 4-Diazepines, synthesis, reactions, biological activities, heterocyclic compounds, biological activities.
Graphical Abstract
[1]
Ramajayam, R.; Giridhar, R.; Yadav, M.R. Current scenario of 1,4-diazepines as potent biomolecules--a mini review. Mini Rev. Med. Chem., 2007, 7(8), 793-812.
[2]
Pathak, V.N.; Joshi, R.; Gupta, N. Synthesis, spectral studies and antimicrobial activityof 7-chloro-2-alkyl/aryl-4-alkyl/aryl-3-arylidene-3H-1,5-benzodiazepine. Indian J. Chem., 2007, 46B, 1191-1997.
[3]
Pant, U.C.; Chandra, H.; Goyal, S.; Pant, S. Synthesis and antimicrobial studies of 10-substituted-6a,7-dihydro-6h-7-(4-fluorophenyl)-6-phenyl[1] benzopyrano[3,4c][1,5] benzothi-zepines. Indian J. Chem., 2006, 45B, 752-757.
[4]
Toth, G.; Halsaz, J.; Levai, A. Conformational analysis of 2,3-dihydro-2,2-dimethyl-1,4-benzoxazepines and their 1,5-isomers. Monatsh. Chem., 1997, 128, 625-632.
[5]
Thomas, L.L.; Arthur, R.H. The Synthesis of Oxazolo- and Oxazino[3,2-d] [1,4]benzodiazepinones. J. Heterocycl. Chem., 1971, 8, 125-128.
[6]
Walser, A.; Zenchoff, G. Quinazolines and 1,4-benzodiazepines LXXXII. reaction of 2-hydrazino-benzodiazepines with 1,3-diearbonyl compounds. J. Heterocycl. Chem., 1978, 15, 161-163.
[7]
Martinez, R.; Angeles, E.; Maya, B.; Cogordon, J.A.; Martinez, L.; Posada, M.E.; Toscano, A.; Del, M.; Arellano, R.; Espinosa, R.C. Synthesis of purinobenzodiazepine and purinobenzotriazocine derivatives, two new heterocyclic ring systems. J. Heterocycl. Chem., 1999, 36, 639-642.
[8]
Melani, F.; Cecchi, L.; Colotta, V.; Filacchioni, G. Tricyclic heteroaromatic systems. 5H-1,2,3-triazolo[5,1-c][1,4]benzodiazepine. J. Heterocycl. Chem., 1989, 26, 1605-1609.
[9]
Bertelli, L.; Biagi, G.; Giorgi, I.; Livi, O.; Manera, C.; Scartoni, V.; Martini, C.; Giannaccini, G.; Trincavelli, L.; Barili, P.L. 1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a]-[1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding. Farmaco, 1998, 53(4), 305-311.
[10]
Pardo, L.M.; Tellitu, I.; Domínguez, E. A versatile PIFA-mediated approach to structurally diverse pyrrolo(benzo)diazepines from linear alkynylamides. Tetrahedron, 2010, 60, 5811-5818.
[11]
Remers, W.A. Pyrrolo(1,4)benzodiazepines.In: The Chemistry of Anti-tumor Antibiotics; John Wiley: New York, 1988.
[12]
Thurston, D.E.; Bose, D.S. Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines. Chem. Rev., 1994, 94, 433-465.
[13]
Hadjivassileva, T.; Thurston, D.E.; Taylor, P.W. Pyrrolobenzodiazepine dimers: novel sequence-selective, DNA-interactive, cross-linking agents with activity against Gram-positive bacteria. J. Antimicrob. Chemother., 2005, 56(3), 513-518.
[14]
Venkatesan, A.M.; Grosu, G.T.; Failli, A.A.; Chan, P.S.; Coupet, J.; Saunders, T.; Mazandarani, H.; Ru, X. (4-Substituted-phenyl)-(5H-10,11-dihydro-pyrrolo [2,1-c][1,4] benzodiazepin-10-yl)-methanone derivatives as vasopressin receptor modulators. Bioorg. Med. Chem. Lett., 2005, 15(22), 5003-5006.
[15]
Kumar, R.; Lown, J.W. Design, synthesis and in vitro cytotoxic studies of novel bis-pyrrolo[2,1][1,4] benzodiazepine-pyrrole and imidazole polyamide conjugates. Eur. J. Med. Chem., 2005, 40(7), 641-654.
[16]
Masterson, L.A.; Spanswick, V.J.; Hartley, J.A.; Begent, R.H.; Howard, P.W.; Thurston, D.E. Synthesis and biological evaluation of novel pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy. Bioorg. Med. Chem. Lett., 2006, 16(2), 252-256.
[17]
Wang, J.J.; Shen, Y.K.; Hu, W.P.; Hsieh, M.C.; Lin, F.L.; Hsu, M.K.; Hsu, M.H. Design, synthesis, and biological evaluation of pyrrolo[2,1-c][1,4]benzodiazepine and indole conjugates as anticancer agents. J. Med. Chem., 2006, 49(4), 1442-1449.
[18]
Antonow, D.; Jenkins, T.C.; Howard, P.W.; Thurston, D.E. Synthesis of a novel C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione library: Effect of C2-aryl substitution on cytotoxicity and non-covalent DNA binding. Bioorg. Med. Chem., 2007, 15(8), 3041-3053.
[19]
Kamal, A.; Khan, M.N.A.; Reddy, K.S.; Ahmed, S.K.; Kumar, M.S.; Juvekar, A.; Sen, S.; Zingde, S. 1,2,4-benzothiadiazine linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: Synthesis, DNA-binding affinity and cytotoxicity. Bioorg. Med. Chem. Lett., 2007, 17(19), 5345-5348.
[20]
Kamal, A.; Kumar, P.P.; Seshadri, B.N.; Srinivas, O.; Kumar, M.S.; Sen, S.; Kurian, N.; Juvekar, A.S.; Zingde, S.M. Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: Synthesis, DNA-binding affinity and cytotoxicity. Bioorg. Med. Chem., 2008, 16(7), 3895-3906.
[21]
Leimgruber, W.; Stefanović, V.; Schenker, F.; Karr, A.; Berger, J. Isolation and characterization of anthramycin, a new antitumor antibiotic. J. Am. Chem. Soc., 1965, 87(24), 5791-5793.
[22]
Meerpoel, L.; Van Gestel, J.; Van Gerven, F.; Woestenborghs, F.; Marichal, P.; Sipido, V.; Terence, G.; Nash, R.; Corens, D.; Richards, R.D. Pyrrolo[1,2-a][1,4]benzodiazepine: A novel class of non-azole anti-dermatophyte anti-fungal agents. Bioorg. Med. Chem. Lett., 2005, 15(14), 3453-3458.
[23]
Krezel, I.; Mikiciuk, O.E.; Zurek, E.; Glowka, M.L. New mitoguazone analogues with anticancer activity. Pharm. Pharmacol. Commun., 1999, 5, 485-490.
[24]
Narayana, B.; Vijaya Raj, K.K.; Ashalatha, B.V.; Kumari, N.S. Synthesis of some new substituted triazolo [4,3-a][1,4] benzodiazepine derivatives as potent anticonvulsants. Eur. J. Med. Chem., 2006, 41(3), 417-422.
[25]
Massa, S.; Corelli, F.; Artico, M.; Mai, A.; Silvestri, R.; Pantaleoni, G.C.; Palumbo, G.; Fanini, D.; Giorgi, R. 5-Aroyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepin-4-carboxylic acids: synthesis and analgesic and neurobehavioral activity. Farmaco, 1989, 44(2), 109-123.
[26]
Hara, T.; Kayama, Y.; Mori, T.; Itoh, K.; Fujimori, H.; Sunami, T.; Hashimoto, Y.; Ishimoto, S. Diazepines. 5. Synthesis and biological action of 6-phenyl-4H-pyrrolo[1,2-a][1,4]benzodiazepines. J. Med. Chem., 1978, 21(3), 263-268.
[27]
Massa, S.; Artico, M.; Mai, A.; Corelli, F.; Botta, M.; Tafi, A.; Pantaleoni, G.C.; Giorgi, R.; Coppolino, M.F.; Cagnotto, A. Pyrrolobenzodiazepines and related systems. 2. Synthesis and biological properties of isonoraptazepine derivatives. J. Med. Chem., 1992, 35(24), 4533-4541.
[28]
Glamkowski, E.J.; Chiang, Y. Tetracyclic benzodiazepines. 4. Synthesis of the novel benzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepine ring system, and derivatives with potential antipsychotic activity. J. Heterocycl. Chem., 1987, 24, 1599-1604.
[29]
Massa, S.; Artico, M.; Mai, A.; Corelli, F.; Pantaleoni, G.C.; Giorgi, R.; Ottaviani, D.; Cagnotto, A. Pyrrolobenzodiazepine and related systems. I. Synthesis and pharmacological evaluation of new 5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine derivatives. Farmaco, 1990, 45(12), 1265-1281.
[30]
Corelli, F.; Massa, S.; Stefancich, G.; Ortenzi, G.; Artico, M.; Pantaleoni, G.C.; Palumbo, G.; Fanini, D.; Giorgi, R. Benzodiazepines with both sedative and analgesic activities. Eur. J. Med. Chem., 1986, 21, 445-449.
[31]
Usdin, E.; Tallman, J.F.; Skolnick, P.; Greenblatt, D.; Paul, S.M. Pharmacology of Benzodiazepines; John Wiley: New York, 1983.
[32]
Hindmarch, I.; Beaumont, G.; Brandon, S.; Leonard, B.L. Benzodiazepines: Current Concepts Biological, Clinical and Social Perspectives; John Wiley: New York, 1990.
[34]
Curtis, M.P.; Dwight, W.; Pratt, J.; Cowart, M.; Esbenshade, T.A.; Krueger, K.M.; Fox, G.B.; Pan, J.B.; Pagano, T.G.; Hancock, A.A.; Faghih, R.; Bennani, Y.L. D-amino acid homopiperazine amides: Discovery of A-320436, a potent and selective non-imidazole histamine H(3)-receptor antagonist. Arch. Pharm. (Weinheim), 2004, 337(4), 219-229.
[35]
Kawakami, Y.; Kitani, H.; Yuasa, S.; Abe, M.; Moriwaki, M.; Kagoshima, M.; Terasawa, M.; Tahara, T. Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antago-nists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system. Eur. J. Med. Chem., 1996, 31, 683-692.
[36]
Spencer, K.; Santosh, N.; Resnick, L. Synthesis of the liposidomycin diazepanone. Tetrahedron Lett., 1992, 33, 5485-5486.
[37]
Kato, S.; Harada, H.; Morie, T. Efficient synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepine from methyl (2R)- and (2S)-1-benzyloxycarbonylaziridine-2-carboxylates. J. Chem. Soc., Perkin Trans. 1, 1997, 1997, 3219-3226.
[38]
Ramajayam, R.; Giridhar, R.; Yadav, M.R. Synthesis of novel substituted diaryl-1, 4-diazepines. Chem. Heterocycl. Compd., 2006, 42(7), 901-906.
[39]
Hirokawa, Y.; Fujiwara, I.; Suzuki, K.; Harada, H.; Yoshikawa, T.; Yoshida, N.; Kato, S. Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotonin 5-HT3 and dopamine D2 receptor antagonistic activity. J. Med. Chem., 2003, 46(5), 702-715.
[40]
Taillefumier, C.; Thielges, S.; Chapleur, Y. Anomeric spiroannelated 1,4-diazepine 2,5-diones from furano exo-glycals: Towards a new class of spironucleosides. Tetrahedron, 2004, 60, 2213-2224.
[41]
Lakatosh, S.A.; Luzikov, Y.N.; Preobrazhenskaya, M.N. Synthesis of 6H-pyrrolo[3′,4′:2,3][1,4]diazepino[6,7,1-hi]indole-8,10(7H,9H)-diones using 3-bromo-4-(indol-1-yl)maleimide scaffold. Org. Biomol. Chem., 2003, 1(5), 826-833.
[42]
Levin, J.I.; DiJoseph, J.F.; Killar, L.M.; Sung, A.; Walter, T.; Sharr, M.A.; Roth, C.E.; Skotnicki, J.S.; Albright, J.D. The synthesis and biological activity of a novel series of diazepine MMP inhibitors. Bioorg. Med. Chem. Lett., 1998, 8(19), 2657-2662.
[43]
Janin, Y.L.; Aubertin, A.M.; Chiaroni, A.; Riche, C.; Monneret, C.; Bisagani, E.; Grierson, D.S. Imidazo[1,5-g][1,4]diazepines, TIBO analogues lacking the phenyl ring: Synthesis and evaluation as Anti-HIV agents. Tetrahedron, 1996, 52, 15157-15170.
[44]
Cobo, J.; Nogueras, M.; Low, J.N.; Rodriguez, R. Bischler-Napieralski cyclocondensation in the synthesis of new 11H-pyrimido[4,5-b][1,4]benzodiazepines. Tetrahedron Lett., 2008, 49, 7271-7273.
[45]
Jeon, M-K.; Kwon, J-J.; Kim, M-S.; Gong, Y-D. A novel solid-phase synthetic method for 1,4-benzodiazepine-2,5-dione derivatives. Synlett, 2008, 2008, 1651-1656.
[46]
Ghomi, S.J.; Hatami, A. Facile and efficient one-pot protocol for synthesis of 5-phenyl 1,4-benzodiazepine-2-one derivatives. Synth. Commun., 2008, 38, 297-302.
[47]
Cabedo, N.; Pannecoucke, X.; Quirion, J.C. An efficient asymmetric synthesis of 2-substituted 1,4-benzodiazepin-3-one as a potential molecular scaffold. Eur. J. Org. Chem., 2005, 1590-1596.
[48]
Marcaccini, S.; Miliciani, M.; Pepino, R. A facile synthesis of 1,4-benzodiazepine derivatives via Ugi four-component condensation. Tetrahedron Lett., 2005, 46, 711-711.
[49]
Wiklund, P.; Rogers-Evans, M.; Bergman, J. Synthesis of 1,4-benzodiazepine-3,5-diones. J. Org. Chem., 2004, 69(19), 6371-6376.
[50]
Shachi, S.; Man, M.; Ashutosh, S. Synthesis and spectral characterization of 1,4-diazepines from 7-aminocephalosporanic acid and their biological activity. Int. J. Rec. Res. Rev., 2012, 2, 10-15.
[51]
Rajesh, K.; Yogesh, C. Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety. J. Chem. Sci., 2009, 121, 497-502.
[52]
A, Hamed. O.; Mehdawi, N.; Abu Taha, A.; M Hamed, E.; A Al-Nuri, M.; S. Hussein, A. Synthesis and antibacterial activity of novel curcumin derivatives containing heterocyclic moiety. Iran. J. Pharm. Res., 2013, 12(1), 47-56.
[53]
Saini, R.; Joshi, Y.; Joshi, P. Synthesis and spectral studies of novel diazepine derivatives and study in specific reference to tautomerization. Chem. Sci. Trans., 2013, 2, 1250-1255.
[54]
Joshi, Y.; Shalini, S. Kavita.; Joshi, P.; Rajesh, K. Silica sulfuric acid as a mild and efficient reagent for the synthesis of 1,4-diazepine and 1,5-benzodiazepine derivatives. J. Korean. Chem. Soc., 2011, 55, 638-643.
[55]
Rajesh, K.; Yogesh, J. Synthesis, spectral studies and biological activity of novel 1H-1,4-diazepine derivatives. Indian J. Chem. Sect. B, 2010, 49, 84-88.
[56]
Pavel, S.; Pavel, T.; Svetlana, S.; Anna, Z.; Oscar, K.; Elisa, V.; Maria, D.; Claudio, E. Porphyrazines with annulated diazepine rings. 4. Synthesis and properties of MgII tetradiazepinoporphyrazine carrying exocyclic styryl fragments. J. Porphyr. Phthalocyanines, 2012, 16, 968-976.
[57]
Stroganova, T.A.; Butin, A.V.; Vasilin, V.K.; Nevolina, T.A.; Gennady, D. A new strategy for pyrrolo[1,2-a][1,4]diazepine structure formation. Synlett, 2007, 2007, 1106-1108.
[58]
Butin, A.V.; Nevolina, T.A.; Shcherbinin, V.A.; Trushkov, I.V.; Cheshkov, D.A.; Krapivin, G.D. Furan ring opening-pyrrole ring closure: A new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines. Org. Biomol. Chem., 2010, 8(14), 3316-3327.
[59]
Mohammad, M.; Mehdi, A.; Mina, S.; Zahra, R.; Hooman, M.; Alireza, F.; Abbas, S. Synthesis of novel 1,4-benzodiazepine-3,5-dione derivatives: Reaction of 2-aminobenzamides under Bargellini reaction conditions. Synlett, 2012, 23, 2521-2525.
[60]
Eyad, A.; Ahmad, H.; Mitchell, M.; Frank, F. Synthesis of 2-amino-1,4-benzodiazepin-5-ones from 2-nitrobenzoic acid and α-aminonitriles. ARKIVOC, 2011, 2, 322-330.
[61]
Zia-Ul-Haq, M.; Hameed, S. Duddeck, H.; Ahmed, R. Synthesis of 1, 4-diazepine nucleosides. Turk. J. Chem., 2002, 26(6), 807-815.
[62]
Abuel-Magd, A.; Shorbgi, A.; Hussein, M.; Hamdy, M.; Alim, A. New 1,4-disustituted-6-hydroxyperhydro-1,4-diazepine-2,3-dione derivatives. Bull. Pharm. Sci., 2004, 27, 193-202.
[63]
Lloyd, D.; Scheibelein, W.; Hideg, K. Further studies of the mixture obtained from reactions between conjugated enones and ethylenediamine, and from conjugated enones and 1-aminopropane. J. Chem. Res. Synop., 1981, 3, 62-63.
[64]
Sarda, S.; Jadhav, W.; Kolhe, N.; Landge, M.; Pawar, R. Solvent free one pot synthesis of benzo-[b]-1,4-diazepines using reusable sulfamic acid catalyst. J. Iran. Chem. Soc., 2009, 6, 477-482.
[65]
Mohmoud, A.A.; Mohamed, M.Y.; Shams, H.A. Microwave assisted synthesis of benzodiazepine derivatives: As non-nucleoside anti HIV analogue. J. Chem. Acta., 2012, 1, 35-39.
[66]
Aastha, P.; Priyanka, R.; Anshu, A.; Shashi, S.; Kishore, D. Synthesis of benzoazepino incorporated analogues of 1, 5-benzodiazepine of medicinal interest. Int. J. Chem. Pharm. Sci., 2013, 4, 44-47.
[67]
Briel, D.; Rudolph, I.; Unverferth, K.; Mann, S. Synthesis of disubstituted 1,4-diazepines with affinity to GABAA-receptor subtypes. Pharmazie, 2010, 65(9), 641-644.
[68]
Kamal, M. Condensation of 1-(dicyanomethylene)acenaphthene-2-one with aromatic diamines. J. Chin. Chem. Soc. (Taipei), 2008, 55, 1050-1055.
[69]
Wu, Z.; Ercole, F.; FitzGerald, M.; Perera, S.; Riley, P.; Campbell, R.; Pham, Y.; Rea, P.; Sandanayake, S.; Mathieu, M.N.; Bray, A.M.; Ede, N.J. Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide SynPhase lanterns. J. Comb. Chem., 2003, 5(2), 166-171.
[70]
Deng, X.; Yang, Q.; Kwiatkowski, N.; Sim, T.; McDermott, U.; Settleman, J.E.; Lee, J.D.; Gray, N.S. Discovery of a benzo[e]pyrimido-[5,4-b][1,4]diazepin-6(11H)-one as a Potent and Selective Inhibitor of Big MAP Kinase 1. ACS Med. Chem. Lett., 2011, 2(3), 195-200.
[71]
Fader, L.D.; Landry, S.; Morin, S.; Kawai, S.H.; Bousquet, Y.; Hucke, O.; Goudreau, N.; Lemke, C.T.; Bonneau, P.; Titolo, S.; Mason, S.; Simoneau, B. Optimization of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of HIV capsid assembly inhibitors 1: addressing configurational instability through scaffold modification. Bioorg. Med. Chem. Lett., 2013, 23(11), 3396-3400.
[72]
Pasha, M.A.; Jayashankara, V.P. An expeditious synthesis of 1,5-benzodiazepines derivatives catalyzed by p-toluenesulfonic acid. J. Pharm. Toxicol., 2006, 6, 573-578.
[73]
Shaabani, A.; Maleki, A. Fast and efficient method for the synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions. Iran. J. Chem. Chem. Eng., 2007, 26, 93-97.
[74]
Varala, R.; Enugala, R.; Adapa, S.R. p-nitrobenzoic acid promoted synthesis of 1,5-benzodiazepine derivatives. J. Braz. Chem. Soc., 2007, 18, 291-296.
[75]
Shi, R.X.; Liu, Y.K.; Xu, Z.Y. Sodium tetrachloroaurate(III) dihydrate-catalyzed efficient synthesis of 1,5-benzodiazepine and quinoxaline derivatives. J. Zhejiang Univ. Sci. B, 2010, 11(2), 102-108.
[76]
More, U.B.; Kharat, R.S.; Mahulikar, P.P. An efficient synthesis of 1,5-benzodiazepines using AlCl3 under solvent free condition. Asian J. Chem., 2011, 23, 4311.
[77]
Konda, S.G.; Shaikh, B.M.; Chavan, S.A.; Dawane, B.S. Polyethylene glycol (PEG-400): An efficient and recyclable reaction medium for the synthesis of novel 1,5-benzodiazepines and their antimicrobial activity. Chin. Chem. Lett., 2011, 22, 65-68.
[78]
Herbert, J.A.L.; Suschitzky, H. Synthesis of heterocyclic compounds. part XXIX. substituted 2,3-dihydro-1h-1,5-benzodiazepines. J. Chem. Soc., Perkin Trans. 1, 1974, 2657-2661.
[79]
Morales, H.R.; Ulbarela, B.A.; Contreras, R. New synthesis of dihydro- and tetrahydro-1,5-benzodiazepines by reductive condensation of o-phenylenediamine and ketones in the presence of sodium borohydride. Heterocycles, 1986, 24, 135-139.
[80]
Jung, D.I.; Choi, T.W.; Kim, Y.Y.; Kim, I.S.; Park, Y.M.; Lee, Y.G.; Jung, D.H. Synthesis of 1,5-benzodiazepine derivatives. Synth. Commun., 1999, 29, 1941-1951.
[81]
Balakrishna, M.S.; Kaboudin, B. A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface. Tetrahedron Lett., 2001, 42, 1127-1129.
[82]
Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O. Ytterbium triflate promoted synthesis of 1, 5-benzodiazepine derivatives. Tetrahedron Lett., 2001, 42, 3193-3195.
[83]
Kaboudin, B.; Navaee, K. Alumina/phosphorus pentoxide (APP) as an efficient reagent for the synthesis of 1,5-benzodiazepines under microwave irradiation. Heterocycles, 2001, 55, 1443-1446.
[84]
Pozarentzi, M.; Stephanatou, J.S.; Tsoleridis, C.A. An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation wihout solvent. Tetrahedron Lett., 2002, 43, 1755-1758.
[85]
Yadav, J.S.; Reddy, B.V.S.; Eshwaraiah, B.; Anuradha, K. Amberlyst-15: A novel and recyclable reagent for the synthesis of 1,5-benzodiazepines in ionic liquids. Green Chem., 2002, 4, 592-594.
[86]
Jarikote, D.V.; Siddiqui, S.A.; Rajagopal, R.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. Room temperature ionic liquid promoted synthesis of 1,5-benzodiazepine derivatives under ambient conditions. Tetrahedron Lett., 2003, 44, 1835-1838.
[87]
Sabitha, G.; Reddy, G.S.K.; Reddy, K.B.; Reddy, N.M.; Yadav, J.S.A. New, efficient and environmentally benign protocol for the synthesis of 1,5-benzodiazepines using cerium (III) chloride/sodium iodide supported on silica gel. Adv. Synth. Catal., 2004, 346, 921-923.
[88]
Yadav, J.S.; Reddy, B.V.S.; Kumar, S.P.; Nagaiah, K. Indium(III) bromide: a novel and efficient reagent for the rapid synthesis of 1,5-benzodiazepines under solvent-free conditions. Synthesis, 2005, 480-484.
[89]
De, S.K.; Gibbs, R.A. Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepine derivatives. Tetrahedron Lett., 2005, 46, 1811-1813.
[90]
Reddy, B.M.; Sreekanth, M.; Lakshmanan, P. Sulfated zirconia as an efficient catalyst for organic synthesis and transformation reactions. J. Mol. Catal. Chem., 2005, 237, 93-100.
[91]
Yadav, J.S.; Reddy, B.V.S.; Satheesh, G.; Srinivasulu, G.; Kunwar, A.C. InCI3-catalyzed stereoselective synthesis of optically pure 1,5-benzodiazepines. ARKIVOC, 2005, 3, 221-227.
[92]
Varala, R.; Ramu, E.; Sreelatha, N.; Adapa, S.R. Ceric ammonium nitrate (CAN) promoted efficient synthesis of 1,5-benzodiazepine derivatives. Synlett, 2006, 1009-1014.
[93]
Pasha, M.A.; Jayashankara, V.P. Synthesis of 1,5-benzodiazepine derivatives catalyzed by zinc chloride. Heterocycles, 2006, 68, 1017-1023.
[94]
Khodaei, M.M.; Bahrami, K.; Nazarian, Z. TCT as a rapid and efficient catalyst for the synthesis of 1,5-benzodiazepines. Bull. Korean Chem. Soc., 2008, 29, 1280-1282.
[95]
Ashok, S.; Radhakrishnan, T.; Kishan, H.; Yuvraj, S.; Sunil, K. Mild and efficient phosphonitrilic chloride mediated synthesis for 1,5-denzodizepines. Int. J. Sci. Res. Pub., 2013, 3, 1-7.
[96]
Heshmatollah, A.; Mahmood, T.; Mohammad, N.; Saeed, B. An efficient and green protocol for the synthesis of 1,5-benzodiazepine and quinoxaline derivatives using protic pyridinium ionic liquid as a catalyst. World Appl. Sci. J., 2013, 22, 1711-1717.
[97]
Akshdeep, S.; Rajesh, S. Rapid and efficient synthesis of 2,3-dihydro-1H-1,5-benzodiazepines catalyzed by chloroacetic acid screened among various aliphatic acids under solvent free conditions. Chem. Sci. Trans., 2013, 2, 176-180.
[98]
Kuo, C.W.; Wang, C.C.; Kavala, V.; Yao, C.F. Efficient TCT-catalyzed synthesis of 1,5-benzodiazepine derivatives under mild conditions. Molecules, 2008, 13(9), 2313-2325.
[99]
Zimmer, H.; Librera, C.; Hausner, S.; Baure, J.; Amer, A. Novel 4-aroyl-3-alkoxy-2(5H)-furanones as precursors for the preparation of furo[3, 4-b][1, 4]-diazepine ring system. Molecules, 2008, 8, 735-743.
[100]
Bapat, B.; Shah, V.; Ghadage, R.; Shirote, P. Synthesis of fused [1, 4]-diazepines by base catalysed condensation of 1, 2-diamines with carbonyl compounds. Int. J. Pharm. Sci. Res., 2011, 2, 2328-2331.
[101]
Kaoua, R.; Bennamane, N.; Bakhta, S.; Benadji, S.; Rabia, C.; Nedjar-Kolli, B. Synthesis of substituted 1,4-diazepines and 1,5-benzodiazepines using an efficient heteropolyacid-catalyzed procedure. Molecules, 2010, 16(1), 92-99.
[102]
Haddadi, Z.; Meghezzi, H.; Kaoua, R.; Nedjar-Kolli, B. Theoretical study of 1, 4-diazepines synthesis: The reaction mechanism and tautomerism in gas phase and in solution. Int. J. Pharm. Chem. Biol. Sci., 2013, 3, 470-479.
[103]
Vatsala, S.; Meenakshi, S.; Anshu, A.; Dharma, K. Exploration of newer possibilities to the synthesis of diazepine and quinoline carboxylic acid derivatives. J. Chem., 2013, 2013, 1-8.
[104]
Pardo, L.M.; Tellitu, I.; Domínguez, E. A versatile PIFA-mediated approach to structurally diverse pyrrolo(benzo) diazepines from linear alkynylamides. Tetrahydron., 2010, 66, 5811-5818.
[105]
Moure, A.; Orzáez, M.; Sancho, M.; Messeguer, A. Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors. Bioorg. Med. Chem. Lett., 2012, 22(23), 7097-7099.
[106]
Sati, B.; Sati, H.; Saklani, S.; Bhatt, P.C.; Mishra, R. Synthesis of the impurities during the manufacture of bulk drug midazolam and separation of these impurities by HPLC. Acta Pharm., 2013, 63(3), 385-396.
[107]
Basavaraja, K.; Vaidya, V.; Chandrashekher, C. Synthesis of benzofuro[3,2-e]-1,4-diazepines of pharmacological interest. E-J. Chem., 2008, 5, 567-571.
[108]
Bonacorso, G.; Lourega, V.; Deon, D.; Zanatta, N.; Martins, P. The first synthesis of dihydro-3H-pyrido[2,3-b][1,4]diazepinols and a new alternative approach for diazepinone analogues. Tetrahedron Lett., 2007, 48, 4835.
[109]
Chuang, C.; Bo, J.; Shu-Jiang, T.; Guigen, L. [4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives. Green Chem., 2011, 13, 2107-2115.
[110]
Meenakshi, A. Expedient protocol for the synthesis of isoxazole, pyrazole, pyrimidine derivatives and their medicinal importance. Int. J. Pharm. Res. Biomed. Sci., 2013, 2, 258-269.
[111]
Loudni, L.; Roche, J.; Potiron, V.; Clarhaut, J.; Bachmann, C.; Gesson, J-P.; Tranoy-Opalinski, I. Design, synthesis and biological evaluation of 1,4-benzodiazepine-2,5-dione-based HDAC inhibitors. Bioorg. Med. Chem. Lett., 2007, 17(17), 4819-4823.
[113]
Naim, A.; Khaled, S.; Mohammad, I.; Sami, T. A facile synthesis of quinazolino[1,4]benzodiazepine alkaloids via reductive n-heterocyclization of N-(2-nitrobenzoyl)amides: Total synthesis of asperlicin C, circumdatin H, and analogues. ARKIVOC, 2008, 9, 282-292.
[114]
Süli-Vargha, H.; Schlosser, G.; Ilas, J. 1,4-diazepine-2,5-dione ring formation during solid phase synthesis of peptides containing aspartic acid β-benzyl ester. J. Pept. Sci., 2007, 13(11), 742-748.
[115]
Ramanathan, S.K.; Keeler, J.; Lee, H.L.; Reddy, D.S.; Lushington, G.; Aubé, J. Modular synthesis of cyclic peptidomimetics inspired by γ-turns. Org. Lett., 2005, 7(6), 1059-1062.
[116]
Fenster, E.; Rayabarapu, D.K.; Zhang, M.; Mukherjee, S.; Hill, D.; Neuenswander, B.; Schoenen, F.; Hanson, P.R.; Aubé, J. Three-component synthesis of 1,4-diazepin-5-ones and the construction of γ-turn-like peptidomimetic libraries. J. Comb. Chem., 2008, 10(2), 230-234.
[117]
Kaur, N.; Kishore, D. Application of chalcones in heterocycles synthesis: synthesis of 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues of 1,4-benzodiazepin-5-carboxamides linked through an oxyphenyl bridge. J. Chem. Sci., 2013, 125, 555-560.
[118]
Mibu, N.; Yukawa, M.; Kashige, N.; Iwase, Y.; Goto, Y.; Miake, F.; Yamaguchi, T.; Ito, S.; Sumoto, K. Synthesis and DNA strand breakage activity of some 1,4-diazepines. Chem. Pharm. Bull. (Tokyo), 2003, 51(1), 27-31.
[119]
Ramajayam, R.; Rajani, G.; Yadav, M. Synthesis of novel substituted diaryl-1,4-diazepines. Chem. Het. Comp., 2006, 42, 901-906.
[120]
Jerry, J.; Ray, B.; Yathirajan, H.; Narayana, B.; Prakash, K. 5,7-Dimethyl-2,3-dihydro-1H-1,4-diazepin-4-ium picrate. Acta Crystallogr., 2010, E66, 01187-01188.
[121]
Nagaraju, G.; Madhava, R.; Jithan, V. Synthesis and evaluation of clozapine and its related compounds. Int. J. Pharm. Sci. Nanotech., 2010, 2, 762-767.
[122]
Liszkiewicz, H.; Nawrocka, W.P.; Sztuba, B.; Wietrzyk, J.; Jaroszewicz, J.; Nasulewicz, A.; Pełczyńska, M. Synthesis and antiproliferative activity in vitro of new pyrido[1,4-b]diazepine derivatives and imidazo[4,5-b]pyridine. Acta Pol. Pharm., 2011, 68(3), 349-355.
[123]
Gholamhassan, I.; Zahra, A.; Yaser, S. Synthesis and conformational analysis of new derivatives of 7-chloro-1,3-dihydro-5-phenyl-2h-1,4-benzodiazepine-2-one. Org. Chem. Ind. J., 2012, 8, 293-298.
[124]
Weber, K.H.; Kuhn, F.J.; Böke-Kuhn, K.; Lehr, E.; Danneberg, P.B.; Hommer, D.; Paul, S.M.; Skolnick, P. Pharmacological and neurochemical properties of 1,4-diazepines with two annelated heterocycles (‘hetrazepines’). Eur. J. Pharmacol., 1985, 109(1), 19-31.
[125]
Gaggini, F.; Laleu, B.; Orchard, M.; Fioraso-Cartier, L.; Cagnon, L.; Houngninou-Molango, S.; Gradia, A.; Duboux, G.; Merlot, C.; Heitz, F.; Szyndralewiez, C.; Page, P. Design, synthesis and biological activity of original pyrazolo-pyrido-diazepine, -pyrazine and -oxazine dione derivatives as novel dual Nox4/Nox1 inhibitors. Bioorg. Med. Chem., 2011, 19(23), 6989-6999.
[126]
Leonard, K.; Marugan, J.J.; Raboisson, P.; Calvo, R.; Gushue, J.M.; Koblish, H.K.; Lattanze, J.; Zhao, S.; Cummings, M.D.; Player, M.R.; Maroney, A.C.; Lu, T. Novel 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists with improved cellular activity. Bioorg. Med. Chem. Lett., 2006, 16(13), 3463-3468.
[127]
Parks, D.J.; Lafrance, L.V.; Calvo, R.R.; Milkiewicz, K.L.; Gupta, V.; Lattanze, J.; Ramachandren, K.; Carver, T.E.; Petrella, E.C.; Cummings, M.D.; Maguire, D.; Grasberger, B.L.; Lu, T. 1,4-Benzodiazepine-2,5-diones as small molecule antagonists of the HDM2-p53 interaction: Discovery and SAR. Bioorg. Med. Chem. Lett., 2005, 15(3), 765-770.
[128]
Parks, D.J.; LaFrance, L.V.; Calvo, R.R.; Milkiewicz, K.L.; Marugán, J.J.; Raboisson, P.; Schubert, C.; Koblish, H.K.; Zhao, S.; Franks, C.F.; Lattanze, J.; Carver, T.E.; Cummings, M.D.; Maguire, D.; Grasberger, B.L.; Maroney, A.C.; Lu, T. Enhanced pharmacokinetic properties of 1,4-benzodiazepine-2,5-dione antagonists of the HDM2-p53 protein-protein interaction through structure-based drug design. Bioorg. Med. Chem. Lett., 2006, 16(12), 3310-3314.
[129]
Marugan, J.J.; Leonard, K.; Raboisson, P.; Gushue, J.M.; Calvo, R.; Koblish, H.K.; Lattanze, J.; Zhao, S.; Cummings, M.D.; Player, M.R.; Schubert, C.; Maroney, A.C.; Lu, T. Enantiomerically pure 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists. Bioorg. Med. Chem. Lett., 2006, 16(12), 3115-3120.
[130]
Dai, Y.; Chen, N.; Wang, Q.; Zheng, H.; Zhang, X.; Jia, S.; Dong, L.; Feng, D. Docking analysis and multidimensional Hybrid QSAR model of 1,4-benzodiazepine-2,5-diones as HDM2 antagonists. Iran. J. Pharm. Res., 2012, 11(3), 807-830.
[131]
Gill, R.K.; Kaushik, S.O.; Chugh, J.; Bansal, S.; Shah, A.; Bariwal, J. Recent development in [1,4]benzodiazepines as potent anticancer agents: A review. Mini Rev. Med. Chem., 2014, 14(3), 229-256.
[132]
Moure, A.; Orzáez, M.; Sancho, M.; Messeguer, A. Synthesis of enantiomerically pure perhydro-1,4-diazepine-2,5-dione and 1,4-piperazine-2,5-dione derivatives exhibiting potent activity as apoptosis inhibitors. Bioorg. Med. Chem. Lett., 2012, 22(23), 7097-7099.
[133]
Sabatié, A.; Végh, D.; Loupy, A.; Floch, L. Synthesis of aromatic and heteroaromatic annelated [1, 4] diazepines. ARKIVOC, 2001, 6, 122-128.
[134]
Kaoua, R.; Bennamane, N.; Bakhta, S.; Benadji, S.; Rabia, C.; Nedjar-Kolli, B. Synthesis of substituted 1,4-diazepines and 1,5-benzodiazepines using an efficient heteropolyacid-catalyzed procedure. Molecules, 2010, 16(1), 92-99.
[135]
Kamal, A.; Srikanth, Y.V.V.; Ramaiah, M.J.; Khan, M.N.A.; Kashi Reddy, M.; Ashraf, M.; Lavanya, A.; Pushpavalli, S.N.; Pal-Bhadra, M. Synthesis, anticancer activity and apoptosis inducing ability of bisindole linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates. Bioorg. Med. Chem. Lett., 2012, 22(1), 571-578.
Call for Papers in Thematic Issues
31 December, 2024
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
27 April, 2024
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
Article Metrics
88
5
1
1