3-(p-acetamidophenylthio)propanol | 78234-10-3

• 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: 3-(p-acetamidophenylthio)propanol
• 英文别名: N-[4-(3-hydroxypropylsulfanyl)phenyl]acetamide
• CAS: 78234-10-3
• 化学式: C₁₁H₁₅NO₂S
• mdl: MFCD12179156
• 分子量: 225.312
• InChiKey: FSULDRSWSQYWLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(p-acetamidophenylthio)propanol 在 吡啶 、 氯化亚砜 作用下， 以 ice-water 、 二氯甲烷 为溶剂， 生成 γ-chloropropyl 4-acetamidophenyl sulfide
  参考文献：
  名称：

  Inhibitor of dihydrofolate reductase

  摘要：

  一组含有芳基-Z-烷氧基-5-苄基嘧啶的化合物已经通过2,4-二氨基-5-苄基嘧啶与芳基-Z-烷基卤代物或取代的环氧乙烷进行烷基化反应而制备出来。这些化合物是有效的二氢叶酸还原酶（DHFR）抑制剂，可用作抗菌、抗原虫和抗肿瘤剂。

  公开号：

  US04258045A1
• 作为产物：
  描述：

  N-{4-[(3-oxopropyl)sulfanyl]phenyl}acetamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3-(p-acetamidophenylthio)propanol
  参考文献：
  名称：

  Novel thiol-based TACE inhibitors. Part 2: Rational design, synthesis, and SAR of thiol-containing aryl sulfones

  摘要：

  A series of potent thiol-containing aryl sulfone TACE inhibitors were designed and synthesized. The SAR and MMP selectivity of the series were investigated. In particular, compound 8b showed excellent in vitro potency against the isolated enzyme and good selectivity over MMP-2, -7, -8, -9, and -13. The X-ray structure of 8b in complex with TACE was also obtained.

  DOI：

  10.1016/j.bmcl.2007.11.014

文献信息

• US4258045A
  申请人：——

  公开号：US4258045A

  公开（公告）日：1981-03-24
• Novel thiol-based TACE inhibitors. Part 2: Rational design, synthesis, and SAR of thiol-containing aryl sulfones
  作者：Upul K. Bandarage、Tiansheng Wang、Jon H. Come、Emanuele Perola、Yunyi Wei、B. Govinda Rao

  DOI：10.1016/j.bmcl.2007.11.014

  日期：2008.1

  A series of potent thiol-containing aryl sulfone TACE inhibitors were designed and synthesized. The SAR and MMP selectivity of the series were investigated. In particular, compound 8b showed excellent in vitro potency against the isolated enzyme and good selectivity over MMP-2, -7, -8, -9, and -13. The X-ray structure of 8b in complex with TACE was also obtained.
• Inhibitor of dihydrofolate reductase
  申请人：Merck & Co., Inc.

  公开号：US04258045A1

  公开（公告）日：1981-03-24

  A group of aryl-Z-alkoxy-5-benzylpyrimidines wherein Z is oxy, thio, imino, carbonyl, carbamoyl, sulfonyl, sulfinyl or sulfamoyl has been prepared from 2,4-diamino-5-benzylpyrimidine via alkylation with either an aryl-Z-alkyl halide or a substituted glycidyl ether. These compounds are potent dihydrofolate reductase (DHFR) inhibitors which are useful as antibacterial, anti-protozoal and antitumor agents.

  一组含有芳基-Z-烷氧基-5-苄基嘧啶的化合物已经通过2,4-二氨基-5-苄基嘧啶与芳基-Z-烷基卤代物或取代的环氧乙烷进行烷基化反应而制备出来。这些化合物是有效的二氢叶酸还原酶（DHFR）抑制剂，可用作抗菌、抗原虫和抗肿瘤剂。