4-(2-mercaptothiazol-4-yl)benzoic acid | 189152-64-5

• 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: 4-(2-mercaptothiazol-4-yl)benzoic acid
• 英文别名: 4-(2-sulfanylidene-3H-1,3-thiazol-4-yl)benzoic acid
• CAS: 189152-64-5
• 化学式: C₁₀H₇NO₂S₂
• 分子量: 237.303
• InChiKey: MLPDMHHZENVEGO-UHFFFAOYSA-N

物化性质

• 沸点：
  450.1±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-mercaptothiazol-4-yl)benzoic acid 在 palladium on activated charcoal MOPS buffer 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8
• 作为产物：
  描述：

  4-乙酰基苯甲酸 在 三氯化铝 、 溴 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 23.5h， 生成 4-(2-mercaptothiazol-4-yl)benzoic acid
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8

文献信息

• Cephem compounds and pharmaceutical use thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06150351A1

  公开（公告）日：2000-11-21

  This invention relates to new cephem compound represented by the following general formula (I): ##STR1## wherein each symbol is as defined in the specification or a salt thereof, which has antimicrobial activity against Helicobacter pylori, and are useful as anti-Helicobacter pylori agents, anti-gastritis agents, anti-ulcer agents and anti-cancer agents.

  本发明涉及一种由以下一般式（I）表示的新头孢素化合物：其中每个符号如规范中定义或其盐，具有抗幽门螺杆菌活性，并可用作抗幽门螺杆菌药物、抗胃炎药物、抗溃疡药物和抗癌药物。
• [EN] NEW CEPHEM COMPOUNDS AND PHARMACEUTICAL USE THEREOF<br/>[FR] NOUVEAUX COMPOSES DE CEPHEM ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1997029111A1

  公开（公告）日：1997-08-14

  (EN) This invention relates to new cephem compounds represented by general formula (I) wherein each symbol is as defined in the specification or a salt thereof, which has antimicrobial activity against $i(Helicobacter pylori), and are useful as anti-$i(Helicobacter pylori) agents, anti-gastritis agents, anti-ulcer agents and anti-cancer agents.(FR) Cette invention concerne un nouveau composé de céphem représenté par la formule générale (I) dans laquelle chaque symbole est tel que défini dans la description. Cette invention concerne également les sels de ce composé, lequel possède une activité antimicrobienne dirigée contre l'$i(Helicobacter pylori). Ce composé est utile en qualité d'agent de lutte contre l'$i(Helicobacter pylori), les gastrites, les ulcères et le cancer.

  该发明涉及新的头孢菌素化合物，由通式（I）表示，其中每个符号如规范中所定义或其盐，具有抗菌活性，可用作抗$ i（幽门螺杆菌）剂，抗胃炎剂，抗溃疡剂和抗癌剂。该化合物对$ i（幽门螺杆菌）具有抗菌活性，因此对于治疗幽门螺杆菌感染、胃炎、溃疡和癌症等方面具有重要作用。
• NEW CEPHEM COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0882052A1

  公开（公告）日：1998-12-09
• US6150351A
  申请人：——

  公开号：US6150351A

  公开（公告）日：2000-11-21
• Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems
  作者：Hisatoshi Shinagawa、Hiroshi Yamaga、Hitoshi Houchigai、Yoshihiro Sumita、Makoto Sunagawa

  DOI：10.1016/s0968-0896(96)00273-8

  日期：1997.3

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.