(4-but-2-ynyloxyphenylsulfanyl)acetic acid ethyl ester | 287201-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-but-2-ynyloxyphenylsulfanyl)acetic acid ethyl ester
• 英文别名: (4-but-2-ynyloxy-phenylsulfanyl)-acetic acid ethyl ester；Ethyl 2-(4-but-2-ynoxyphenyl)sulfanylacetate
• CAS: 287201-52-9
• 化学式: C₁₄H₁₆O₃S
• 分子量: 264.345
• InChiKey: VZGMAJYXMRVMNO-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  393.6±37.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-but-2-ynyloxyphenylsulfanyl)acetic acid ethyl ester 在 oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 以96%的产率得到(4-but-2-ynyloxybenzenesulfonyl)acetic acid ethyl ester
  参考文献：
  名称：

  ALKYNYL CONTAINING HYDROXAMIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MATRIX METALLOPROTEINASE (MMP) INHIBITORS / TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS

  摘要：

  公开号：

  EP1147085B1
• 作为产物：
  描述：

  ethyl 2-((4-hydroxyphenyl)thio)acetate 、 1-溴-2-丁炔 在 potassium carbonate 作用下， 反应 8.0h， 以96%的产率得到(4-but-2-ynyloxyphenylsulfanyl)acetic acid ethyl ester
  参考文献：
  名称：

  ALKYNYL CONTAINING HYDROXAMIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MATRIX METALLOPROTEINASE (MMP) INHIBITORS / TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS

  摘要：

  公开号：

  EP1147085B1

文献信息

• Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/TACE inhibitors
  申请人：WYETH

  公开号：US20040229924A1

  公开（公告）日：2004-11-18

  Compounds of the formula: 1 useful in the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection.

  该式的化合物：1在治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周病、骨病、糖尿病（胰岛素抵抗）和HIV感染方面有用。
• Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors
  申请人：American Cyanamid Company

  公开号：US20020086890A1

  公开（公告）日：2002-07-04

  Compounds of the formula: 1 useful in the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection.

  以下公式化合物：1，对于治疗关节炎、肿瘤转移、组织溃疡、异常伤口愈合、牙周疾病、骨疾病、糖尿病（胰岛素抵抗）和HIV感染非常有用。
• Synthesis and Structure−Activity Relationships of 4-alkynyloxy Phenyl Sulfanyl, Sulfinyl, and Sulfonyl Alkyl Hydroxamates as Tumor Necrosis Factor-α Converting Enzyme and Matrix Metalloproteinase Inhibitors
  作者：Aranapakam M. Venkatesan、Jamie M. Davis、George T. Grosu、Jannie Baker、Arie Zask、Jeremy I. Levin、John Ellingboe、Jerauld S. Skotnicki、John F. DiJoseph、Amy Sung、Guixian Jin、Weixin Xu、Diane Joseph McCarthy、Dauphine Barone

  DOI：10.1021/jm040086x

  日期：2004.12.1

  A series of 4-alkynyloxy phenyl sulfanyl, sulfinyl and sulfony alkyl and piperidine-4-carboxylic acid hydroxamides were synthesized. Their structure-activity relationships, against tumor necrosis factor-alpha (TACE) and matrix metalloproteinase (NIMP) inhibitor activities, are presented by investigating the oxidation state on sulfur and altering the P1' substituent. The sulfonyl derivatives 20-24 carrying a 4-butynyloxy moiety were selective TACE inhibitors over the MMPs tested. The sulfinyl derivatives showed a preference for a specific oxidation on sulfur as in compounds 25-28. The selectivity over MMPs was also demonstrated in the sulfonyl series. The enhanced cellular activity was achieved upon incorporating a butynyloxy substituent in the piperidene series. Compounds 64 and 65 were potent inhibitors of TNF-alpha release in the mouse at 100 mg/kg po.
• US6358980B1
  申请人：——

  公开号：US6358980B1

  公开（公告）日：2002-03-19
• US6753337B2
  申请人：——

  公开号：US6753337B2

  公开（公告）日：2004-06-22