Synthesis of new 2-alkyl-5-arylimino-2,5-dihydroisothiazole derivatives

被引：1

作者：

Skrastina, I. ^{[1
]}

Baran, A. ^{[1
]}

Muceniece, D. ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 49卷 / 04期

关键词：

2-alkyl-5-arylimino-2,5-dihydroisothiazoles; 2-substituted N-arylamides of 2-alkylaminobut-2-enethioic acid; enamine-imine tautomerism; oxidative cyclization; UBER ISOTHIAZOLE; BENZOTHIAZOLES; CYTOTOXICITY; CYCLIZATION;

D O I：

10.1007/s10593-013-1290-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization of 2-substituted N-arylamides of 3-alkylaminobut-2-enethioic acid gave a series of new 2-alkyl-5-arylimino-2,5-dihydroisothiazole derivatives containing a benzoyl or ester group at position 4. A study was carried out on the course of this reaction in the presence of various oxidizing agents, including halogens, N-bromosuccinimide, hydrogen peroxide. Some of the isothiazoles obtained in this work exhibited cytotoxic activity against both normal and cancer cell lines.

引用

页码：624 / 635

页数：12

共 50 条

[21] Cobalt(II) nitrate promoted cyclization of benzoyl hydrazone for the synthesis of 2,5-diphenyl-1,3,4-oxadiazole derivatives
Li, Xiaojun
Liao, Shangtie
Chen, Yu
Xia, Chengcai
Wang, Guodong
JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (11-12) : 1038 - 1041
[22] Synthesis and Spectral Study of a New Family of 2,5-Diaryltriazoles Having Restricted Rotation of the 5-Aryl Substituent
Tsyrenova, Biligma
Nenajdenko, Valentine
MOLECULES, 2020, 25 (03):
[23] Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2, 4-thiazolidinedione derivatives
Patil, Vijay
Tilekar, Kalpana
Mehendale-Munj, Sonali
Mohan, Rhea
Ramaa, C. S.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (10) : 4539 - 4544
[24] 4-Alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2-oxaphosphole 2-Oxides: Synthesis and 1,3-Cycloaddition
Brel, Valery K.
Alekseychuk, Ekaterina P.
Artyushin, Oleg I.
Anikina, Lada V.
SYNTHESIS-STUTTGART, 2022, 54 (07): : 1823 - 1832
[25] Synthesis, antimycobacterial screening and molecular docking studies of 4-aryl-4′-methyl-2′-aryl-2,5′-bisthiazole derivatives
Abhale, Yogita K.
Shinde, Abhijit D.
Deshmukh, Keshav K.
Nawale, Laxman
Sarkar, Dhiman
Choudhari, Prafulla B.
Kumbhar, Santosh S.
Mhaske, Pravin C.
MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (11) : 2889 - 2899
[26] Synthesis, antimycobacterial screening and molecular docking studies of 4-aryl-4′-methyl-2′-aryl-2,5′-bisthiazole derivatives
Yogita K. Abhale
Abhijit D. Shinde
Keshav K. Deshmukh
Laxman Nawale
Dhiman Sarkar
Prafulla B. Choudhari
Santosh S. Kumbhar
Pravin C. Mhaske
Medicinal Chemistry Research, 2017, 26 : 2889 - 2899
[27] Synthesis and Cytotoxic Evaluation of 2-O-alkyl Derivatives of L-Ascorbic Acid
Dengale, Rohit A.
Thopate, Shankar R.
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 27 (04) : 395 - 399
[28] Synthesis of 2,5-disubstituted-1,4-benzoquinone derivatives as potential antimicrobial and cytotoxic agents
Hassan, MA
Maslat, AO
Abussaud, M
Ahmed, IC
AlKofahi, AS
ARCHIV DER PHARMAZIE, 1998, 331 (12) : 385 - 388
[29] Photochromic dihetarylethenes. 12.* Synthesis of 5-alkyl-2- (1,3,4-oxadiazol-2-yl)thiophenes and their photochromic derivatives
Krayushkin M.M.
Stoyanovich F.M.
Zolotarskaya O.Yu.
Chernoburova E.I.
Makhova N.N.
Yarovenko V.N.
Zavarzin I.V.
Martynkin A.Yu.
Uzhinov B.M.
Chemistry of Heterocyclic Compounds, 2002, 38 (02) : 165 - 176
[30] Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts
Qu, Bo
Mangunuru, Hari P. R.
Wei, Xudong
Fandrick, Keith R.
Desrosiers, Jean-Nicolas
Sieber, Joshua D.
Kurouski, Dmitry
Haddad, Nizar
Samankumara, Lalith P.
Lee, Heewon
Savoie, Jolaine
Ma, Shengli
Grinberg, Nelu
Sarvestani, Max
Yee, Nathan K.
Song, Jinhua J.
Senanayake, Chris H.
ORGANIC LETTERS, 2016, 18 (19) : 4920 - 4923

← 1 2 3 4 5 →