ethyl 4-methyl-2-(phenylsulfonamido)thiazole-5-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-methyl-2-(phenylsulfonamido)thiazole-5-carboxylate
• 英文别名: 2-benzenesulfonylamino-4-methyl-thiazole-5-carboxylic acid ethyl ester；2-Benzolsulfonylamino-4-methyl-thiazol-5-carbonsaeure-aethylester；ethyl 2-(benzenesulfonamido)-4-methyl-1,3-thiazole-5-carboxylate
• 化学式: C₁₃H₁₄N₂O₄S₂
• 分子量: 326.397
• InChiKey: JHTYHGMKCMJKMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-2-(phenylsulfonamido)thiazole-5-carboxylate 生成 2-benzenesulfonylamino-4-methyl-thiazole-5-carboxylic acid
  参考文献：
  名称：

  Sprague; Lincoln; Ziegler, Journal of the American Chemical Society, 1946, vol. 68, p. 268

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 、 苯磺酰氯 在 吡啶 作用下， 反应 48.0h， 以77%的产率得到ethyl 4-methyl-2-(phenylsulfonamido)thiazole-5-carboxylate
  参考文献：
  名称：

  噻唑羧酸衍生物。1. N-取代的2-氨基-4-甲基噻唑-5-羧酸衍生物

  摘要：

  DOI：

  10.1023/b:cohc.0000023773.23834.ba

文献信息

• Synthesis of novel 2-arylsulfonylimino-3,4- dimethyl-5-(5-<i>S</i>-substituted [1,3,4]oxadiazol- 2-yl)-2,3-dihydrothiazole derivatives and their plant growth stimulant activity
  作者：Karine A. Eliazyan、Ruzanna S. Hakobyan、Vergush A. Pivazyan、Emma A. Ghazaryan、Siranush V. Harutyunyan、Aleksandr P. Yengoyan

  DOI：10.1515/hc-2013-0055

  日期：2013.8.1

  two-step synthesis. Heterocyclization of the hydrazide moiety yielded 2-arylsulfonylimino-3,4-dimethyl-5-(5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-2,3-dihydro-thiazoles 3. Treatment of compounds 3 with various alkyl halides gave corresponding S-substituted derivatives 4–6. The plant growth stimulant activities of synthesized compounds were compared with those of similar [1,2,4]triazol- and [1,3,4,]th

  摘要 2-芳基磺酰基亚氨基-3,4-二甲基-2,3-二氢噻唑-5-羧酸酰肼2由相应的2-芳基磺酰基亚氨基-4-甲基-2,3-二氢噻唑-5-羧酸乙酯1在a两步合成。酰肼部分的杂环化产生 2-芳基磺酰基亚氨基-3,4-二甲基-5-(5-thioxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-2,3-dihydro-thiazoles 3. 用各种卤代烷处理化合物 3 得到相应的 S-取代衍生物 4-6。将合成化合物的植物生长刺激活性与类似的 [1,2,4] 三唑和 [1,3,4,]噻二唑-2-基-噻唑进行比较。
• Bifunctional ethyl 2-amino-4-methylthiazole-5-carboxylate derivatives: Synthesis and in vitro biological evaluation as antimicrobial and anticancer agents
  作者：Sherif A.F. Rostom、Hassan M. Faidallah、Mohammed F. Radwan、Mona H. Badr

  DOI：10.1016/j.ejmech.2014.02.027

  日期：2014.4

  Thirty thiazole compounds bearing chemotherapeutically-active pharmacophores were synthesized and evaluated for their preliminary in vitro antimicrobial and anticancer activities. Nineteen compounds displayed obvious antibacterial potential, with special bactericidal activity against Gram positive bacteria, whereas, nine analogs showed moderate to weak antifungal activity against Candida albicans. The analog 12f proved to be the most active antimicrobial member identified in this study being comparable to ampicillin and gentamicin sulfate against Staphylococcus aureus and Bacillus subtilis, together with a moderate antifungal activity. Additionally, nine derivatives were tested for their preliminary in vitro anticancer activity according to the current one-dose protocol of the NCI. Compound 9b revealed a broad spectrum of anticancer activity against 29 out of the tested 60 subpanel tumor cell lines. Collectively, compounds 4, 9b, 10b and 12f could be considered as promising dual anticancer antibiotics. (C) 2014 Elsevier Masson SAS. All rights reserved.