Main Article Content
Abstract
Purpose: A new series of benzodiazepine and benzothiazepine annulated derivatives of carbazolo condensed azepinones were synthesized.
Methodology: Synthesis was done through a one-pot approach. The structure of these compounds was established based on their analytical IR, 1H NMR, 13C NMR and mass spectral data. The antimicrobial activity of the synthesized drugs was evaluated by the disc diffusion method.
Main Findings: The activity index and zone of inhibition were also examined in comparison to standard drugs fluconazole and streptomycin. The synthesized compound has gained much importance due to its diverse biological activities.
Implications: One-pot method is a highly innovative strategy, which has been easy to operate, requires inexpensive material and in applying to a wide range of functionalized substrates.
Keywords
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References
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- Braccio, M. D., Grossi, G., Roma, G., Vargiu, L., Mura, M. & Marongiu, M. E. (2001). 1,5-benzodiazepines. Part: XII: synthesis and biological evaluation of tricyclic and tetracyclic 1,5-benzodiazepine derivatives of niverapine analogues. European journal of medicinal chemistry, 36(11), 935. https://doi.org/10.1016/S0223-5234(01)01283-1
- Cherkupally, S. R., Gurrala, P. R., Adki, N. & Avula, S. (2008). Synthesis and biological study of novel methylene-bis benzofuranyl-1,5-benzothizepines. ChemInform, 4, 84. https://doi.org/10.1002/chin.200804172
- Devi, T. K., Achaiah, G. & Reddy, V. M. (1988). Synthesis of 6-alkyl/aryl-5, 11-dihydro-9-nitro [1] benzopyrano[2,3-b] [1,5] benzodiazepine-1,3-ones as possible antipsychotic agents. Journal of the Indian Chemical Society, 65, 567-570. https://doi.org/10.1002/chin.198907228
- Di Braccio, M., Grossi, G., Roma, G., Vargiu, L., Mura, M., & Marongiu, M. E. (2001). 1, 5-Benzodiazepines. Part XII. Synthesis and biological evaluation of tricyclic and tetracyclic 1, 5-benzodiazepine derivatives as nevirapine analogues. European journal of medicinal chemistry, 36(11-12), 935-949.https://doi.org/10.1016 /S0223-5234(01)01283-1
- Fryer, R. I. (1991). Bicyclic Diazepines, In Comprehensive Heterocyclic Chemistry, ed: E.C. Taylor, Wiley, New York. 50, Chapter II. https://doi.org/10.1002/9780470187371
- Ganjali, M. R., Razavi, T. & Dinarvend, R. (2008). New ditiazam potentiometric membrane sensor stand on theoretical calculation as a useful device for ditiazam hydrochloride analysis in pharmaceutical formulation and urine. International Journal of Electrochemical Science, 3, 1543.
- Grandolini, G., Perioli, L. & Ambrogi, V. (1999). Synthesis of some new 1,4-benzothiazepines and 1,5-benzothiazepine tricyclic derivatives with the structural analogy with TIBO and their screening for anti-HIV activity. European journal of medicinal chemistry, 34(9), 701. https://doi.org/10.1016/S0223-5234(99)00223-8
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- Hussenether, T., Hübner, H., Gmeiner, P., & Troschütz, R. (2004). Clozapine derived 2, 3-dihydro-1H-1, 4-and 1, 5-benzodiazepines with D4 receptor selectivity: synthesis and biological testing. Bioorganic & medicinal chemistry, 12(10), 2625-2637.https://doi.org/10.1016/j.bmc.2004.03.023.
- Inagaki, K., Kihara, Y., Izumi, T. & Sasayama, S. (2000). The cardioprotective effects of a new 1,4-benzothiazepine derivative, JTV519, on ischemia/reperfusion-induced Ca2+ overload in isolated rat hearts. Cardiovascular Drugs and Therapy, 14, 489-495. https://doi.org/10.1023/A:1007884905461
- Kamal, A., Shankaraiah, N., Prabhakar, S., Reddy, C. R., Markandeya, N., Laxma K. & Devaiah, X. (2008). Solid-phase synthesis of new pyrrolobenzodiazepine-chalcone conjugates: DNA-binding affinity and anticancer activity. Bioorganic & Medicinal Chemistry Letters, 18, 2434-2439. https://doi.org/10.1016/j.bmc l.2008.02.047.
- Kamble, R. R. & Subha, B. S. (2008). Synthesis and Pharmacological Evaluation of 1,5-benzothiazepine derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 183, 1691. https://doi.org/10.1080 /10426500701724555
- Kavali, J. R., & Badami, B. V. (2000). 1, 5-Benzodiazepine derivatives of 3-arylsydnones: synthesis and antimicrobial activity of 3-aryl-4-[2′-aryl-2′, 4′, 6′, 7′-tetrahydro-(1′ H)-1′, 5′-benzodiazepine-4′-yl] sydnones. II Farmaco, 55(5), 406-409.https://doi.org/10.1016/S0014-827X(00)00061-6
- Kuch, H. (1979). Chemical aspects of 1,4 and 1,5-benzodiazepines. British Journal of Clinical Pharmacology, 7, 175. https://doi.org/10.1111/j.1365-2125.1979.tb04659.x.
- Kumar, R., & Joshi, Y. C. (2007). Synthesis, spectral studies and biological activity of 3H-1, 5-benzodiazepine derivatives. Arkivoc, 13, 142-149.https://doi.org/10.3998/ark.5550190.0008.d17
- Mane, R. A. & Ingle, D. B. (1983). Synthesis and biological activity of some new 1,5-benzothiazepines containing thiazole moiety-2-aryl-4-(4'-methyl-2-substituted-aminothiazo-5-yl)-2,3-dihydro-1,5-benzothiazepine. Chemischer Informationsdienst, 14, 27. https://doi.org/10.1002/chin.198327263
- Nagao, T., Asto, M. & Iwasawa, Y. (1973). Studied on a new 1,5-benzothiazepine derivative (crd-401) iii. Effects of optical isomers of crd-401 on smooth muscles and other pharmacological properties. Japanese Journal of Pharmacology, 22, 467. https://doi.org/10.1016/S0021-5198(19)31644-0
- Narayana, B., Raj, K. V., Ashalatha, B. V., & Kumari, N. S. (2006). Synthesis of some new substituted triazolo [4, 3-a][1, 4] benzodiazepine derivatives as potent anticonvulsants. European journal of medicinal chemistry, 41(3), 417-422.https://doi.org/10.1016/j.ejmech.2005.12.003
- Narta, H., Muruta, S. & Suzuki, T. (1990). Synthesis and pharmacological properties of azido derivatives of benzothiazepine Ca antagonist. Chemical and Pharmaceutical Bulletin, 38, 407. https://doi.org/10.1248/ cpb.38.407.
- Nawrocka, W., Sztuba, B., Opolski, A., Wietrzyk, J., Kowalska, M. W., & Glowiak, T. (2001). Synthesis and Antiproliferative Activity in Vitro of Novel 1, 5â€Benzodiazepines. Part II. Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, 334(1), 3-10. https://doi.org/10.1002/1521-4184(200101)334:1<3::AID-ARDP3>3.0.CO;2-2
- Opera, T. I., Davis, A. M. & Teague, S. J. (2001). Is there a difference between leads and drugs? A historical perspective. Journal of Chemical Information and Computer Sciences, 41, 1308. https://doi.org/10.1021/ci0 10366a.
- Randall, L. O., Schallek, W., Sternbach, L. H., & Ning, R. Y. (1974). Psychopharmacological agents, 175-281. https://doi.org/10.1016/B978-0-12-290558-2.50014-9
- Raval. J. P., Desai, J. T., Desai, C. K. & Desai, K. R. (2008). A comparative study of microwave-assisted and conventional synthesis of 2,3-dihydro-2-aryl-4-oxo-2H-chromen-3-yl-1,3-thiazol-2-ylamino-1,5-benzothiazepines and its antimicrobial activity. ARKIVOC, 12, 233-244. https://doi.org/10.3998/ark.5550190. 0009.c25
- Roma, G., Grossi, G. C., Di Braccio, M., Ghia, M., & Mattioli, F. (1991). 1, 5-Benzodiazepines IX. A new route to substituted 4H-[1, 2, 4] triazolo [4, 3-a][1, 5] benzodiazepin-5-amines with analgesic and/or anti-inflammatory activities. European journal of medicinal chemistry, 26(5), 489-496. https://doi.org/10.1016/ 0223-5234(91)90144-C
- Yamamoto, H., Nakamura, Y. & Kumoh, Y. (1986). Antiulcer effects of -cis-2,3-dihydro-3-(4-methylpiperazinylmethyl)-2-phenyl-1, 5H-one hydrochloride in experimental animals. Japanese Journal of Pharmacology, 41(3), 283. https://doi.org/10.1254/jjp.41.283
References
Beasley, C. M., Tollenfson, G. & Tran, P. (1996). Olanzapine versus placebo and haloperidol: acute phase result of North America double-blind olanzapine trial. Neuropsychopharmacology, 14, 111. https://doi.org/10. 1016/0893-133X(95)00069-P
Braccio, M. D., Grossi, G., Roma, G., Vargiu, L., Mura, M. & Marongiu, M. E. (2001). 1,5-benzodiazepines. Part: XII: synthesis and biological evaluation of tricyclic and tetracyclic 1,5-benzodiazepine derivatives of niverapine analogues. European journal of medicinal chemistry, 36(11), 935. https://doi.org/10.1016/S0223-5234(01)01283-1
Cherkupally, S. R., Gurrala, P. R., Adki, N. & Avula, S. (2008). Synthesis and biological study of novel methylene-bis benzofuranyl-1,5-benzothizepines. ChemInform, 4, 84. https://doi.org/10.1002/chin.200804172
Devi, T. K., Achaiah, G. & Reddy, V. M. (1988). Synthesis of 6-alkyl/aryl-5, 11-dihydro-9-nitro [1] benzopyrano[2,3-b] [1,5] benzodiazepine-1,3-ones as possible antipsychotic agents. Journal of the Indian Chemical Society, 65, 567-570. https://doi.org/10.1002/chin.198907228
Di Braccio, M., Grossi, G., Roma, G., Vargiu, L., Mura, M., & Marongiu, M. E. (2001). 1, 5-Benzodiazepines. Part XII. Synthesis and biological evaluation of tricyclic and tetracyclic 1, 5-benzodiazepine derivatives as nevirapine analogues. European journal of medicinal chemistry, 36(11-12), 935-949.https://doi.org/10.1016 /S0223-5234(01)01283-1
Fryer, R. I. (1991). Bicyclic Diazepines, In Comprehensive Heterocyclic Chemistry, ed: E.C. Taylor, Wiley, New York. 50, Chapter II. https://doi.org/10.1002/9780470187371
Ganjali, M. R., Razavi, T. & Dinarvend, R. (2008). New ditiazam potentiometric membrane sensor stand on theoretical calculation as a useful device for ditiazam hydrochloride analysis in pharmaceutical formulation and urine. International Journal of Electrochemical Science, 3, 1543.
Grandolini, G., Perioli, L. & Ambrogi, V. (1999). Synthesis of some new 1,4-benzothiazepines and 1,5-benzothiazepine tricyclic derivatives with the structural analogy with TIBO and their screening for anti-HIV activity. European journal of medicinal chemistry, 34(9), 701. https://doi.org/10.1016/S0223-5234(99)00223-8
Hagiwara, M., Adachi, S. & Nagao, T. (1997). High-affinity Binding of DTZ323, a novel derivative of ditiazem, to rabbit skeletal muscle L-type Ca Channels. European Journal of Pharmacology, 466(1), 63-71. https://doi.org/10.1016/s0014-2999(03)01547-4
Hussenether, T., Hübner, H., Gmeiner, P., & Troschütz, R. (2004). Clozapine derived 2, 3-dihydro-1H-1, 4-and 1, 5-benzodiazepines with D4 receptor selectivity: synthesis and biological testing. Bioorganic & medicinal chemistry, 12(10), 2625-2637.https://doi.org/10.1016/j.bmc.2004.03.023.
Inagaki, K., Kihara, Y., Izumi, T. & Sasayama, S. (2000). The cardioprotective effects of a new 1,4-benzothiazepine derivative, JTV519, on ischemia/reperfusion-induced Ca2+ overload in isolated rat hearts. Cardiovascular Drugs and Therapy, 14, 489-495. https://doi.org/10.1023/A:1007884905461
Kamal, A., Shankaraiah, N., Prabhakar, S., Reddy, C. R., Markandeya, N., Laxma K. & Devaiah, X. (2008). Solid-phase synthesis of new pyrrolobenzodiazepine-chalcone conjugates: DNA-binding affinity and anticancer activity. Bioorganic & Medicinal Chemistry Letters, 18, 2434-2439. https://doi.org/10.1016/j.bmc l.2008.02.047.
Kamble, R. R. & Subha, B. S. (2008). Synthesis and Pharmacological Evaluation of 1,5-benzothiazepine derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 183, 1691. https://doi.org/10.1080 /10426500701724555
Kavali, J. R., & Badami, B. V. (2000). 1, 5-Benzodiazepine derivatives of 3-arylsydnones: synthesis and antimicrobial activity of 3-aryl-4-[2′-aryl-2′, 4′, 6′, 7′-tetrahydro-(1′ H)-1′, 5′-benzodiazepine-4′-yl] sydnones. II Farmaco, 55(5), 406-409.https://doi.org/10.1016/S0014-827X(00)00061-6
Kuch, H. (1979). Chemical aspects of 1,4 and 1,5-benzodiazepines. British Journal of Clinical Pharmacology, 7, 175. https://doi.org/10.1111/j.1365-2125.1979.tb04659.x.
Kumar, R., & Joshi, Y. C. (2007). Synthesis, spectral studies and biological activity of 3H-1, 5-benzodiazepine derivatives. Arkivoc, 13, 142-149.https://doi.org/10.3998/ark.5550190.0008.d17
Mane, R. A. & Ingle, D. B. (1983). Synthesis and biological activity of some new 1,5-benzothiazepines containing thiazole moiety-2-aryl-4-(4'-methyl-2-substituted-aminothiazo-5-yl)-2,3-dihydro-1,5-benzothiazepine. Chemischer Informationsdienst, 14, 27. https://doi.org/10.1002/chin.198327263
Nagao, T., Asto, M. & Iwasawa, Y. (1973). Studied on a new 1,5-benzothiazepine derivative (crd-401) iii. Effects of optical isomers of crd-401 on smooth muscles and other pharmacological properties. Japanese Journal of Pharmacology, 22, 467. https://doi.org/10.1016/S0021-5198(19)31644-0
Narayana, B., Raj, K. V., Ashalatha, B. V., & Kumari, N. S. (2006). Synthesis of some new substituted triazolo [4, 3-a][1, 4] benzodiazepine derivatives as potent anticonvulsants. European journal of medicinal chemistry, 41(3), 417-422.https://doi.org/10.1016/j.ejmech.2005.12.003
Narta, H., Muruta, S. & Suzuki, T. (1990). Synthesis and pharmacological properties of azido derivatives of benzothiazepine Ca antagonist. Chemical and Pharmaceutical Bulletin, 38, 407. https://doi.org/10.1248/ cpb.38.407.
Nawrocka, W., Sztuba, B., Opolski, A., Wietrzyk, J., Kowalska, M. W., & Glowiak, T. (2001). Synthesis and Antiproliferative Activity in Vitro of Novel 1, 5â€Benzodiazepines. Part II. Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, 334(1), 3-10. https://doi.org/10.1002/1521-4184(200101)334:1<3::AID-ARDP3>3.0.CO;2-2
Opera, T. I., Davis, A. M. & Teague, S. J. (2001). Is there a difference between leads and drugs? A historical perspective. Journal of Chemical Information and Computer Sciences, 41, 1308. https://doi.org/10.1021/ci0 10366a.
Randall, L. O., Schallek, W., Sternbach, L. H., & Ning, R. Y. (1974). Psychopharmacological agents, 175-281. https://doi.org/10.1016/B978-0-12-290558-2.50014-9
Raval. J. P., Desai, J. T., Desai, C. K. & Desai, K. R. (2008). A comparative study of microwave-assisted and conventional synthesis of 2,3-dihydro-2-aryl-4-oxo-2H-chromen-3-yl-1,3-thiazol-2-ylamino-1,5-benzothiazepines and its antimicrobial activity. ARKIVOC, 12, 233-244. https://doi.org/10.3998/ark.5550190. 0009.c25
Roma, G., Grossi, G. C., Di Braccio, M., Ghia, M., & Mattioli, F. (1991). 1, 5-Benzodiazepines IX. A new route to substituted 4H-[1, 2, 4] triazolo [4, 3-a][1, 5] benzodiazepin-5-amines with analgesic and/or anti-inflammatory activities. European journal of medicinal chemistry, 26(5), 489-496. https://doi.org/10.1016/ 0223-5234(91)90144-C
Yamamoto, H., Nakamura, Y. & Kumoh, Y. (1986). Antiulcer effects of -cis-2,3-dihydro-3-(4-methylpiperazinylmethyl)-2-phenyl-1, 5H-one hydrochloride in experimental animals. Japanese Journal of Pharmacology, 41(3), 283. https://doi.org/10.1254/jjp.41.283