Synthesis of novel 1,3-thiazin-4-ones by acetylene diester cyclization and their anticancer activities

被引：5

作者：

Anand, Selvam Athavan Alias ^{[1
]}

Loganathan, Chandrasekaran ^{[1
]}

Thomas, Nisha Susan ^{[2
]}

Saravanan, Kuppusamy ^{[1
]}

Alphonsa, Antony Therasa ^{[1
]}

Kabilan, Senthamaraikannan ^{[1
]}

机构：

[1] Annamalai Univ, Dept Chem, Drug Discovery Lab, Annamalainagar, Tamil Nadu, India

[2] Annamalai Univ, Dept Biochem & Biotechnol, Annamalainagar, Tamil Nadu, India

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2016年 / 191卷 / 10期

关键词：

1,3-Thiazin-4-one; acetylene diesters; in vitro; apoptosis; cytotoxicity; DIMETHYL ACETYLENEDICARBOXYLATE; ALKALOIDS; CHEMISTRY; ANALOGS; RING;

D O I：

10.1080/10426507.2016.1209502

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel series of 1,3-thiazin-4-one derivatives containing a piperidyl ring (7-16) were designed and synthesized efficiently by thioamide and acetylene diester cyclization reaction via aminolysis of the ester group and the elimination of an alcohol molecule. The structures of all the novel compounds were established by their FTIR, Mass, H-1 NMR, and C-13 NMR spectral techniques. The newly synthesized compounds (7-16) were studied for their in vitro anticancer activity against human liver cancer cell lines Hep G2 using MTT assay. The IC50 values of the tested compounds were ranging in between 7.48 +/- 0.71 and 56.57 +/- 1.37 mu M. Further, the apoptosis evaluation by the mitochondrial membrane potential using JC-1 dye was carried out and the results are in good agreement with the cytotoxicity studies. [GRAPHICS] .

引用

页码：1396 / 1401

页数：6

共 19 条

[11] Synthesis of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-ones, their lipophilicity and anticancer activity in vitro [J].

Matysiak, Joanna ;

Juszczak, Malgorzata ;

Karpinska, Monika M. ;

Langner, Ewa ;

Walczak, Katarzyna ;

Lemieszek, Marta K. ;

Skrzypek, Alicja ;

Niewiadomy, Andrzej ;

Rzeski, Wojciech .

MOLECULAR DIVERSITY, 2015, 19 (04) :725-736

[12] SURVEY ON THE PHARMACODYNAMICS OF THE NEW ANTIPSYCHOTIC RISPERIDONE [J].

MEGENS, AAHP ;

AWOUTERS, FHL ;

SCHOTTE, A ;

MEERT, TF ;

DUGOVIC, C ;

NIEMEGEERS, CJE ;

LEYSEN, JE .

PSYCHOPHARMACOLOGY, 1994, 114 (01) :9-23

[13] RAPID COLORIMETRIC ASSAY FOR CELLULAR GROWTH AND SURVIVAL - APPLICATION TO PROLIFERATION AND CYTO-TOXICITY ASSAYS [J].

MOSMANN, T .

JOURNAL OF IMMUNOLOGICAL METHODS, 1983, 65 (1-2) :55-63

[14] Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids [J].

O'Hagan, D .

NATURAL PRODUCT REPORTS, 2000, 17 (05) :435-446

[15] PYRROLE, PYRROLIDINE, PIPERIDINE, PYRIDINE, AND AZEPINE ALKALOIDS [J].

PINDER, AR .

NATURAL PRODUCT REPORTS, 1992, 9 (01) :17-23

[16] Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: anticancer activity evaluation and mode of action study [J].

Thakur, Anuj ;

Manohar, Sunny ;

Gerena, Christian E. Velez ;

Zayas, Beatriz ;

Kumar, Vineet ;

Malhotra, Sanjay V. ;

Rawat, Diwan S. .

MEDCHEMCOMM, 2014, 5 (05) :576-586

[17] REACTION OF 2H-BENZIMIDAZOLE-2-THIONE WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].

WADE, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (11) :1816-1819

[18] RING TRANSFORMATION OF MICHAEL ADDUCTS OF 4-BENZYLIDENE-5-OXAZOLONES AND 3-MERCAPTO-S-TRIAZOLES TO 2,3-DIHYDRO-4H-SYM-TRIAZOLO[3,4-B][1,3]THIAZIN-4-ONES WITH SOME ANTIFUNGAL ACTIVITY [J].

YADAV, LDS ;

MISRA, AR ;

SINGH, H .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (03) :633-636

[19] Suppression of fully kindled seizure and retardation of kindling acquisition by YM928 in the rat kindling model of epilepsy [J].

Yamashita, H ;

Ohno, K ;

Inami, H ;

Shishikura, J ;

Sakamoto, S ;

Okada, M ;

Yamaguchi, T .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2004, 494 (2-3) :147-154

← 1 2 →