Synthesis, In Silico Studies, and Larvicidal Activity of Novel Hydrazinyl 1,3-Thiazine Derivatives

被引：2

作者：

Velidandi, Amarnath ^{[1
]}

Kannuri, Rajeswari ^{[1
]}

Thupurani, Murali Krishna ^{[2
]}

机构：

[1] Chaitanya Deemed Univ, Dept Chem, Warangal 506001, Andhra Pradesh, India

[2] Chaitanya Deemed Univ, Dept Biotechnol, Warangal 506001, Andhra Pradesh, India

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 58卷 / 06期

关键词：

chalcones; thiosemicarbazide; thiazines; in silico studies; larvicidal activity;

D O I：

10.1134/S1070428022060094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Looking at the importance of thiazine derivatives as biologically active compounds, herein we describe the synthesis of 4,6-diaryl-2-hydrazinyl-1,3-thiazines from the corresponding chalcones and thiosemi-carbazide in the presence of sodium hydroxide on heating. The synthesized compounds were tested for their larvicidal activity against saltwater shrimp eggs (Artemia cysts), and some of the compounds showed good to excellent activities. Their in silico drug likeness was estimated.

引用

页码：814 / 819

页数：6

共 11 条

[1] Chemoselective Synthesis of Structurally Diverse 3,4-Dihydroquinazoline-2(1H)-thiones and 4H-Benzo[d][1,3]thiazines [J].

Dong, Jian-Lian ;

Wei, Pei-Shun ;

Yu, Li-Si-Han ;

Xie, Jian-Wu .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :2219-2226

[2] Thiasporines A-C, Thiazine and Thiazole Derivatives from a Marine-Derived Actinomycetospora chlora [J].

Fu, Peng ;

MacMillan, John B. .

JOURNAL OF NATURAL PRODUCTS, 2015, 78 (03) :548-551

[3] Novel Thiazine Substituted 9-Anilinoacridines: Synthesis, Antitumour Activity and Structure Activity Relationships [J].

Kalirajan, R. ;

Gaurav, K. ;

Pandiselvi, A. ;

Gowramma, B. ;

Sankar, S. .

ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2019, 19 (11) :1350-1358

[4] A New Metabolite with a Unique 4-Pyranone-γ-Lactam-1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus [J].

Li, Chun-Shun ;

Ding, Yuanqing ;

Yang, Bao-Jun ;

Miklossy, Gabriella ;

Yin, Hong-Quan ;

Walker, Larry A. ;

Turkson, James ;

Cao, Shugeng .

ORGANIC LETTERS, 2015, 17 (14) :3556-3559

[5] Synthesis of a 6-CF3-Substituted 2-Amino-dihydro-1,3-thiazine β-Secretase Inhibitor by N,N-Diethylaminosulfur Trifluoride-Mediated Chemoselective Cyclization [J].

Oguma, Takuya ;

Anan, Kosuke ;

Suzuki, Shinji ;

Hisakawa, Shinya ;

Takada, Akihiro ;

Ogawa, Masayoshi ;

Kusakabe, Ken-ichi .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (08) :4893-4897

[6]

Pisutthanan Pisutthanan S. S., 2004, Naresuan University Journal, V12 12, P13

[7] Total Synthesis of Thiaplakortone A: Derivatives as Metabolically Stable Leads for the Treatment of Malaria [J].

Pouwer, Rebecca H. ;

Deydier, Sophie M. ;

Phuc Van Le ;

Schwartz, Brett D. ;

Franken, Nicole C. ;

Davis, Rohan A. ;

Coster, Mark J. ;

Charman, Susan A. ;

Edstein, Michael D. ;

Skinner-Adams, Tina S. ;

Andrews, Katherine T. ;

Jenkins, Ian D. ;

Quinn, Ronald J. .

ACS MEDICINAL CHEMISTRY LETTERS, 2014, 5 (02) :178-182

[8] Intramolecular C-O/C-S bond insertion of α-diazoesters for the synthesis of 2-aryl-4H-benzo[d][1,3]oxazine and 2-aryl-4H-benzo[d][1,3]thiazine derivatives [J].

Reddy, B. V. Subba ;

Babu, R. Anji ;

Reddy, M. Ramana ;

Reddy, B. Jagan Mohan ;

Sridhar, B. .

RSC ADVANCES, 2014, 4 (84) :44629-44633

[9] Synthesis and larvicidal activity of indole derivatives against Aedes aegypti (Diptera: Culicidae) [J].

Sousa, Janaina R. ;

Silva, Fabio A. ;

Targanski, Sabrina K. ;

Fazolo, Bruno R. ;

Souza, Jessica M. ;

Campos, Mateus G. ;

Vieira, Lucas C. C. ;

Mendes, Tiago A. de Oliveira ;

Soares, Marcos A. .

JOURNAL OF APPLIED ENTOMOLOGY, 2019, 143 (10) :1172-1181

[10] Cytochathiazines A-C: Three Merocytochalasans with a 2H-1,4-Thiazine Functionality from Coculture of Chaetomium globosum and Aspergillus flavipes [J].

Wang, Wenjing ;

Zeng, Fanrong ;

Bie, Qiong ;

Dai, Chong ;

Chen, Chunmei ;

Tong, Qingyi ;

Liu, Junjun ;

Wang, Jianping ;

Zhou, Yuan ;

Zhu, Hucheng ;

Zhang, Yonghui .

ORGANIC LETTERS, 2018, 20 (21) :6817-6821

← 1 2 →