5-methyl-1,3-thiazole-2-thiol | 17626-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-1,3-thiazole-2-thiol
• 英文别名: 2-Mercapto-5-methyl-thiazol；5-methyl-3H-thiazole-2-thione；2-mercapto-5-methyl-thiazole；5-methylthiazole-2-thiol；5-methyl-3H-1,3-thiazole-2-thione
• CAS: 17626-82-3
• 化学式: C₄H₅NS₂
• 分子量: 131.222
• InChiKey: DDTHRRVQSOEMNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-1,3-thiazole-2-thiol 在 磺酰氯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 2-氯-5-甲基噻唑
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF 2-CHLORO-5-CHLOROMETHYL-THIAZOLE

  摘要：

  公开号：

  EP0873327B1
• 作为产物：
  描述：

  在 甲醇 、 三乙胺 作用下， 生成 5-methyl-1,3-thiazole-2-thiol
  参考文献：
  名称：

  Substituted heterocyclic analogs as selective COX-2 inhibitors in the flosulide class

  摘要：

  Substituted heterocyclic analogs in the Flosulide class were investigated as potential selective . 6-(4-Ethyl-2-thiazolylthio)-5-methanesulfonamido-3H-isobenzofuran-1-one 14 was found to be the optimal compound in the series with superior in vitro and in vivo activities. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00705-7

文献信息

• Design, synthesis and antitumor activity evaluation of trifluoromethyl-substituted pyrimidine derivatives
  作者：Limin Liu、Zhengjie Wang、Chao Gao、Honglin Dai、Xiaojie Si、Yang Zhang、Yaqi Meng、Jiaxin Zheng、Yu Ke、Hongmin Liu、Qiurong Zhang

  DOI：10.1016/j.bmcl.2021.128268

  日期：2021.11

  novel trifluoromethyl-substituted pyrimidine derivatives were designed and synthesized, and the bioactivity against four human tumor cells (PC-3, MGC-803, MCF-7 and H1975) was evaluated by MTT assay. Compound 17v displayed potent anti-proliferative activity on H1975 (IC50 = 2.27 μΜ), which was better than the positive control 5-FU (IC50 = 9.37 μΜ). Further biological evaluation studies showed that compound

  为了寻找高效的抗肿瘤新药，设计合成了一系列新型三氟甲基取代的嘧啶衍生物，并通过MTT评估了对四种人类肿瘤细胞（PC-3、MGC-803、MCF-7和H1975）的生物活性。化验。化合物17v对H1975显示出有效的抗增殖活性（IC 50  = 2.27 μM），优于阳性对照5-FU（IC 50  = 9.37 μM）。进一步的生物学评价研究表明，化合物17v 可诱导H1975细胞凋亡，并将细胞周期阻滞在 G2/M 期。此外，化合物17v通过增加促凋亡蛋白 Bax 和 p53 的表达并下调抗凋亡蛋白 Bcl-2 诱导 H1975 细胞凋亡。此外，化合物17v能够紧密嵌入 EGFR 的活性口袋中。总之，这些结果表明化合物17v具有作为进一步研究的先导化合物的潜力。
• [EN] CARBACEPHEM BETA-LACTAM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES BÊTA-LACTAMES CARBACÉPHÈMES
  申请人：ACHAOGEN INC

  公开号：WO2010123997A1

  公开（公告）日：2010-10-28

  Carbacephem β-lactam antibiotics having chemical structures (I) and (II) are disclosed: including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, R1, R2 and R6 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

  Carbacephem β-内酰胺类抗生素具有化学结构（I）和（II）如下：包括立体异构体、药用可接受的盐、酯和前药，其中Ar2、R1、R2和R6如本文所定义。这些化合物对治疗细菌感染特别有效，尤其是由耐甲氧西林金黄色葡萄球菌引起的感染。
• Synthesis of functionalized thiazoles via attack of heterocyclic nucleophiles on allenyl isothiocyanates
  作者：Baker Jawabrah Al-Hourani、Klaus Banert、Nermeen Gomaa、Kai Vrobel

  DOI：10.1016/j.tet.2008.03.074

  日期：2008.6

  New examples of substituted thiazole derivatives carrying different heterocyclic ring systems at C-2 position were prepared via the reaction of several allenyl isothiocyanates with nucleophiles such as imidazoles, pyrazoles, benzimidazoles, indazole, 1,2,3-triazole, 1,2,4-triazole, and 1H-benzotriazole. Although these allenyl isothiocyanates are very reactive electrophiles and tend to polymerize, the

  通过几种异戊烯基异硫氰酸酯与亲核试剂如咪唑，吡唑，苯并咪唑，吲唑，1,2,3-三唑，1,2,4的反应，制备了在C-2位带有不同杂环系统的取代噻唑衍生物的新例子。 -三唑和1 H-苯并三唑。尽管这些烯丙基异硫氰酸酯是非常活泼的亲电子试剂，并且倾向于聚合，但是噻唑产物的产率介于中等和非常好的之间。反应的区域化学通过NMR和X射线研究证明，表明环境亲核试剂的攻击非常有选择地进行。然而，在某些情况下，产物形成为芳族杂环和非芳族异构体的混合物。后者可以重新排列以产生均匀的芳族噻唑。
• Rearrangement Reactions; 14:Synthesis of Functionalized Thiazoles via Attack of Heteroatom Nucleophiles on Allenyl Isothiocyanates
  作者：Klaus Banert、Baker Jawabrah Al-Hourani、Stefan Groth、Kai Vrobel

  DOI：10.1055/s-2005-872203

  日期：——

  Treatment of allenyl isothiocyanates with sulfur-, oxygen-, nitrogen- or hydride-containing nucleophiles such as propane-2-thiol, thiophenol, hydrogen sulfide, alcohols, phenol or aqueous NaOH, NH3, primary or secondary aliphatic or aromatic amines, N,N,N′,N′-tetramethylguanidine or sodium cyanoborohydride resulted in ring closure to generate thiazoles bearing a functionality at position C-2 in most cases. Moreover, we report the first examples of aromatic thiazole-2-phosphonates prepared by the same strategy using dialkyl or diphenyl phosphites as nucleophiles.

  用含硫、氧、氮或氢化物的亲核物（如丙烷-2-硫醇、噻吩酚、硫化氢、醇、酚或 NaOH、NH3、N,N,N′,N′-四甲基胍或氰基硼氢化钠等含氢化物的亲核剂，在大多数情况下会导致环闭合，生成在 C-2 位具有官能团的噻唑。此外，我们还首次报道了以二烷基或二苯基膦酸盐为亲核剂，通过相同策略制备芳香族噻唑-2-膦酸盐的实例。
• Discovery and structure-activity relationship of a series of 1-carba-1-dethiacephems exhibiting activity against methicillin-resistant Staphylococcus aureus
  作者：Robert J. Ternansky、Susan E. Draheim、Andrew J. Pike、F. William Bell、Sarah J. West、Christopher L. Jordan、C. Y. Ernie Wu、David A. Preston、William Alborn

  DOI：10.1021/jm00066a006

  日期：1993.7

  The synthesis and antimicrobial activity of several new 1-carba-1-dethiacephalosporins is described. The discovery of unique activity of some of the analogues against methicillin-resistant Staphylococcus aureus led to the development of a structure-activity relationship designed to optimize this activity. The results of this investigation along with the pharmacokinetic select compounds are described.

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