4-<5-(acetamidomethyl)furan-2-yl>-2-thioureidothiazole | 129596-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-<5-(acetamidomethyl)furan-2-yl>-2-thioureidothiazole
• 英文别名: 4-(5-Acetylaminomethylfuran-2-yl)-2-thioureidothiazole；N-[[5-[2-(carbamothioylamino)-1,3-thiazol-4-yl]furan-2-yl]methyl]acetamide
• CAS: 129596-42-5
• 化学式: C₁₁H₁₂N₄O₂S₂
• 分子量: 296.374
• InChiKey: XYQHTXBSZZYMMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-<5-(acetamidomethyl)furan-2-yl>-2-thioureidothiazole 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 N-[5-(2-{N'-[2-(3-Methoxy-phenyl)-ethyl]-guanidino}-thiazol-4-yl)-furan-2-ylmethyl]-acetamide
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles

  摘要：

  A series of 2-[(arylalkyl)guanidinol-4-[(5-acetamidomethyl)furan-2-yl]thiazoles and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antimicrobial activity (MIC < 0.1 mu g/mL), compounds 31 and 36 additionally possessed H2 antagonist and gastric antisecretory activities. Though compound 51, an analogue incorporating a methyl group onto the furan nucleus of 36, and compound 54, a positional isomer of 51, also showed potent anti-H. pylori activity, the H2 antagonism profile was eliminated from these compounds. Thus, two types of potent anti-H. pylori agents could be derived from the same scaffold.

  DOI：

  10.1021/jm9900671
• 作为产物：
  描述：

  4-[5-(乙酰氨基甲基)呋喃-2-基]-2-氨基噻唑 在 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 4-<5-(acetamidomethyl)furan-2-yl>-2-thioureidothiazole
  参考文献：
  名称：

  Anti- Helicobacter pylori agents. 2. Structure activity relationships in a new series of 2-alkylguanidino-4-furylthiazoles

  摘要：

  SAR for antimicrobial activity against H. pylori was investigated in a new series of 2-alkylguanidino-4-furylthiazoles. Of the compounds obtained, cyclohexylmethyl and ethoxyethyl derivatives were identified as a novel class of anti-H. pylori agents which possessed potent and selective antimicrobial activity against H. pylori. These compounds also showed gastric antisecretory activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00206-6

文献信息

• Anti-<i>Helicobacter pylori</i> Agents. 1. 2-(Alkylguanidino)-4-furylthiazoles and Related Compounds
  作者：Yousuke Katsura、Tetsuo Tomishi、Yoshikazu Inoue、Kazuo Sakane、Yoshimi Matsumoto、Hirohumi Ishikawa、Hisashi Takasugi

  DOI：10.1021/jm970407n

  日期：1997.8.1

  les and related compounds were synthesized and evaluated for antimicrobial activity against Helicobacter pylori, inhibitory effect on gastric acid secretion, and histamine H2-receptor antagonist activity. Introduction of alkyl substituents on the guanidino moiety resulted in a significant increase in antimicrobial activity, which was associated with the alkyl chain length. Of the compounds obtained

  合成了一系列2-（烷基胍基）-4- [5-（乙酰氨基甲基）呋喃-2-基]噻唑及其相关化合物，并评估了其对幽门螺杆菌的抗菌活性，对胃酸分泌的抑制作用以及组胺H2-受体的抑制作用。拮抗剂活性。在胍基部分上引入烷基取代基导致抗菌活性显着增加，这与烷基链长有关。在获得的化合物中，正己基胍基衍生物13的活性（MIC = 0.11微克/ mL）比未取代的胍基衍生物7提高了250倍。烷基取代的胍基衍生物还显示出胃的抗分泌和H2拮抗剂活性。然而，在这些测定中未发现烷基链长与活性之间的简单相关性。用其他生物等位基团（硫脲，尿素或（二甲基氨基）甲基）取代胍导致丧失所有测试的活性。因此，发现胍基部分对于这一系列化合物的活性是必不可少的。
• Furylthiazoles and their use as H.sub.2 - receptor antagonists and
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05512588A1

  公开（公告）日：1996-04-30

  This invention relates to furylthiazole derivatives represented by the following formula: ##STR1## wherein each symbol is as defined in the specification and pharmaceutically acceptable salts thereof which have antiulcer activity, H.sub.2 -receptor antagonism and antimicrobial activity, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the treatment of ulcer and infectious diseases in human being or animals.

  本发明涉及以下公式所代表的呋喃噻唑衍生物：##STR1## 其中每个符号如规范中定义的，以及具有抗溃疡活性、H.sub.2-受体拮抗作用和抗微生物活性的药学上可接受的盐，以及其制备方法、包含它们的制药组合物以及用于治疗人类或动物的溃疡和传染病的方法。
• Furylthiazole derivatives, processes for the preparation thereof and
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05308857A1

  公开（公告）日：1994-05-03

  The invention relates to compounds of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, A and Q are as described, useful in the treatment of ulcers.

  该发明涉及公式为：##STR1## 其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，A和Q如所述的化合物，对溃疡的治疗有用。
• Furylthiazole derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0355612B1

  公开（公告）日：1994-07-27
• US5308857A
  申请人：——

  公开号：US5308857A

  公开（公告）日：1994-05-03