methyl 2-(4-bromophenyl)-4-methylthiazole-5-carboxylate | 187998-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(4-bromophenyl)-4-methylthiazole-5-carboxylate
• 英文别名: Methyl 2-(4-bromophenyl)-4-methyl-5-thiazolecarboxylate；methyl 2-(4-bromophenyl)-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 187998-67-0
• 化学式: C₁₂H₁₀BrNO₂S
• 分子量: 312.187
• InChiKey: LOOKJAXWRMDXFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-bromophenyl)-4-methylthiazole-5-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以60%的产率得到methyl 2-(4-bromophenyl)-4-(dibromomethyl)thiazole-5-carboxylate
  参考文献：
  名称：

  An investigation of phenylthiazole antiflaviviral agents

  摘要：

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.041
• 作为产物：
  描述：

  2-氯乙酰乙酸甲酯 、 对溴硫代苯甲酰胺 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到methyl 2-(4-bromophenyl)-4-methylthiazole-5-carboxylate
  参考文献：
  名称：

  An investigation of phenylthiazole antiflaviviral agents

  摘要：

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.041

文献信息

• Rhodium Carbene Routes to Oxazoles and Thiazoles. Catalyst Effects in the Synthesis of Oxazole and Thiazole Carboxylates, Phosphonates, and Sulfones
  作者：Baolu Shi、Alexander J. Blake、William Lewis、Ian B. Campbell、Brian D. Judkins、Christopher J. Moody

  DOI：10.1021/jo902256r

  日期：2010.1.1

  Dirhodium tetraacetate catalyzed reaction of α-diazo-β-keto-carboxylates and -phosphonates with arenecarboxamides gives 2-aryloxazole-4-carboxylates and 4-phosphonates by carbene N−H insertion and cyclodehydration. In stark contrast, dirhodium tetrakis(heptafluorobutyramide) catalysis results in a dramatic change of regioselectivity to give oxazole-5-carboxylates and 5-phosphonates. α-Diazo-β-ketosulfones

  四乙酸二丁酯催化α-重氮-β-酮基羧酸酯和-膦酸酯与芳烃酰胺的反应，通过卡宾NH插入和环脱水作用，制得2-芳基恶唑-4-羧酸酯和4-膦酸酯。与之形成鲜明对比的是，四（七氟丁酰胺）四氢吡啶鎓催化作用会导致区域选择性的显着变化，从而产生5-羧酸恶唑酯和5-膦酸酯。α-重氮-β-酮砜的行为相似，在四（七氟丁酰胺）四氢吡啶鎓与羧酰胺的催化反应下生成5-磺酰基恶唑。硫代羧酰胺的类似反应得到相应的噻唑-5-羧酸盐，-膦酸酯和-砜。
• NEW CARBOXAMIDES WITH ANTIFUNGAL ACTIVITY
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0783502A1

  公开（公告）日：1997-07-16
• US5888941A
  申请人：——

  公开号：US5888941A

  公开（公告）日：1999-03-30
• [EN] NEW CARBOXAMIDES WITH ANTIFUNGAL ACTIVITY<br/>[FR] NOUVEAUX CARBOXAMIDES A ACTIVITE ANTIFONGIQUE
  申请人：J. URIACH & CIA. S.A.

  公开号：WO1997005131A1

  公开（公告）日：1997-02-13

  (EN) Compounds of general formula (I) and their salts and solvates are antifungal agents and as such are useful in the treatment of various fungal infections. Pharmaceutical compositions including these compounds and processes for their preparation are also provided.(FR) Les composés de la formule générale (I) et leurs sels et solvates sont des agents antifongiques. Ils sont utiles dans le traitement de différentes infections fongiques. L'invention concerne également des compositions pharmaceutiques comprenant ces composés et des procédés permettant leur préparation.