European Journal of Chemistry 2014, 5(1), 138-143. doi:10.5155/eurjchem.5.1.138-143.924

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


Subhash Yenupuri (1,*) , Agastyaraju Venkata Lakshmi Narasimha Satyanarayana Hariharan (2) , Bharat Kumar Bugata (3) , Divakara Laxman Somayajulu Nori (4)

(1) Department of Chemistry (GIS), Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(2) Gitam Institute of Technology, Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(3) Department of Biochemistry and Bioinformatics, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(4) Department of Chemistry (GIS), Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(*) Corresponding Author

Received: 10 Sep 2013, Accepted: 27 Oct 2013, Published: 31 Mar 2014

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.


Keywords


Cytotoxicity; Podophyllotoxin; 1,5-Benzothiazepines; Antimicrobial activity; Brine shrimp lethality; Agar well diffusion assay

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DOI: 10.5155/eurjchem.5.1.138-143.924

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[1]. Satbir Mor, Savita Nagoria, Suchita Sindhu, Mohini Khatri, Gurdeep Sidhu, Virender Singh
Synthesis of Indane-Based 1,5-Benzothiazepines Derived from 3-Phenyl-2,3-dihydro-1H -inden-1-one and Antimicrobial Studies Thereof
Journal of Heterocyclic Chemistry  54(6), 3282, 2017
DOI: 10.1002/jhet.2948
/


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


How to cite


Yenupuri, S.; Hariharan, A.; Bugata, B.; Nori, D. Eur. J. Chem. 2014, 5(1), 138-143. doi:10.5155/eurjchem.5.1.138-143.924
Yenupuri, S.; Hariharan, A.; Bugata, B.; Nori, D. Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents. Eur. J. Chem. 2014, 5(1), 138-143. doi:10.5155/eurjchem.5.1.138-143.924
Yenupuri, S., Hariharan, A., Bugata, B., & Nori, D. (2014). Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents. European Journal of Chemistry, 5(1), 138-143. doi:10.5155/eurjchem.5.1.138-143.924
Yenupuri, Subhash, Agastyaraju Venkata Lakshmi Narasimha Satyanarayana Hariharan, Bharat Kumar Bugata, & Divakara Laxman Somayajulu Nori. "Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents." European Journal of Chemistry [Online], 5.1 (2014): 138-143. Web. 22 Nov. 2019
Yenupuri, Subhash, Hariharan, Agastyaraju, Bugata, Bharat, AND Nori, Divakara. "Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.1.138-143.924

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