European Journal of Chemistry

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents



Main Article Content

Subhash Yenupuri
Agastyaraju Venkata Lakshmi Narasimha Satyanarayana Hariharan
Bharat Kumar Bugata
Divakara Laxman Somayajulu Nori

Abstract

A series of 2,3-dihydro-2-(susbtituted)-4-(1-methyl-1H-pyrrol-2-yl)-1,5-benzothiazepines (4a-v) have been synthesized evaluated for their in vitro cytotoxicity and antimicrobial activities. Among the tested compounds for cytotoxicity using Brine shrimp lethality assay, compound 4q exhibited significant cytotoxicity at ED50 values 3.45±0.15 µg/mL. This level of activity was found comparable to that of the reference drug podophyllotoxin with ED50 value 3.61±0.17 µg/mL. Antimicrobial activity was assessed using agar well diffusion assay method against selected Gram-positive, Gram-negative and fungal strains. Among the compounds tested, 4q, 4r and 4l were found to be more active with MIC 16-32 µg/mL against all tested microorganisms.


icon graph This Abstract was viewed 1547 times | icon graph Article PDF downloaded 781 times

How to Cite
(1)
Yenupuri, S.; Hariharan, A. V. L. N. S.; Bugata, B. K.; Nori, D. L. S. Microwave Assisted Synthesis and Biological Evaluation of a Series of 1,5-Benzothiazepines As Potential Cytotoxic and Antimicrobial Agents. Eur. J. Chem. 2014, 5, 138-143.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Garg, N.; Chandra, T.; Archana; Jain, A. B.; Kumar, A. Eur. J. Med. Chem. 2010, 45, 1529-1535.
http://dx.doi.org/10.1016/j.ejmech.2010.01.001

[2]. Sarro, G. D.; Chimirri, A.; Sarro, A. D.; Gitto, R.; Grasso, S.; Zappala, M. Eur. J. Med. Chem. 1995, 30, 925-929.
http://dx.doi.org/10.1016/0223-5234(96)88311-5

[3]. Grandolini, G.; Perioli, L.; Ambrogi, V. Eur. J. Med. Chem. 1999, 34, 701-709.
http://dx.doi.org/10.1016/S0223-5234(99)00223-8

[4]. Yamada, S.; Mori, Y.; Morimatsu, K.; Ishizu, Y.; Ozaki, Y.; Yoshioka, R.; Nakatani, T.; Seko, H. J. Org. Chem. 1996, 61, 8586-8590.
http://dx.doi.org/10.1021/jo960950w

[5]. Maayan, S.; Ohad, N. and Soliman, K. Bioorg. Med. Chem. 2005, 13, 433-441.
http://dx.doi.org/10.1016/j.bmc.2004.10.010

[6]. Sharma, G.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2008, 49, 4272-4275.
http://dx.doi.org/10.1016/j.tetlet.2008.04.144

[7]. Sharma, G.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2008, 49, 4269-4271.
http://dx.doi.org/10.1016/j.tetlet.2008.04.146

[8]. Stone, P.; Gibson, R.; Glaser, S.; Dewood, M.; Parker, J.; Kawanishi, D.; Crawford, M.; Messineo, F.; Shook, T.; Raby, K. Circulation 1990, 82, 1962-1972.
http://dx.doi.org/10.1161/01.CIR.82.6.1962

[9]. Aoki, K.; Sato, K.; Kondo, S.; Vamamoto, M. Eur. J. Clin. Pharmacol. 1990, 25, 475-480.
http://dx.doi.org/10.1007/BF00542114

[10]. Kuzelova, M.; Svec, P. Cesk. Farm. 1993, 42, 124-126.

[11]. Alonzo, D.; Allert, J.; Thomas, H.; Darbenzio, A.; Raymond, R.; Joseph, S. C. J. Cardivasc. Pharmacol. 1993, 21, 677-683.
http://dx.doi.org/10.1097/00005344-199304000-00024

[12]. Weiss, K.; Fitscha, P.; Gazso, A.; Gludovacz, D.; Sinzinger, H. Prog. Clin. Biol. Res. 1989, 301, 353-357.

[13]. Hirano, K.; Kamaide, H.; Abe, S.; Nakamusra, M. Br. J. Pharmac. 1990, 101, 173-177.
http://dx.doi.org/10.1111/j.1476-5381.1990.tb12700.x

[14]Belusa, J.; Hruskova, V.; Haas, Z.; Kaminska, Z.; Picha, F.; Dusek, J.; Trefulka, M.; Kysilka, V.; Wojnar, V. Czech, CS 274, 213 (1992); Chem. Abstr. 1992, 118, 2459706.

[15]. Bacon, K. B.; Westwick, J.; Camp, R. D. R. Biochem. Biophys, Res. Commun. 1989, 165(1), 349-354.
http://dx.doi.org/10.1016/0006-291X(89)91076-0

[16]. Vaghy, L. P.; Williams, S. J.; Schwartz, A. Am. J. Cardiol. 1987, 59, 961-966.
http://dx.doi.org/10.1016/0002-9149(87)90170-6

[17]. Gedye, R.; Smith, F.; Westaway, K. C.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279-282.
http://dx.doi.org/10.1016/S0040-4039(00)83996-9

[18]. Patel, V. M.; Desai, K. R. Indian J. Chem. 2004, 43B, 199-201.

[19]. Claisen, L.; Claparede A. Ber. 1881, 14, 2463-2479.

[20]. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31-34.
http://dx.doi.org/10.1055/s-2007-971236

[21]. National Committee for Clinical Laboratory Studies (1998), Performance Standards For Antimicrobial Susceptibility Testing, Eighth Information Supplement, Vilanova (PA), NCCLS, (Publication no NCCLS M 100-58).

[22]. Avupati, V. R.; Yejella, R. P.; Akula, A.; Guntuku, G.; Doddi, B. R.; Vutla, V.; Anagani, S. R.; Adimulam, L. S.; Vyricharla, A. K. Bioorg. Med. Chem. Lett. 2012, 22, 6442‐6450.
http://dx.doi.org/10.1016/j.bmcl.2012.08.052

[23]. Avupati, V. R.; Yejella, R. P.; Guntuku, G.; Gunta, P. Bioorg. Med. Chem. Lett. 2012, 22, 1031‐1035.
http://dx.doi.org/10.1016/j.bmcl.2011.11.125

Supporting Agencies

Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).