2-(3-乙氧基-4-甲氧基苯基)乙硫醇 | 396088-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(3-乙氧基-4-甲氧基苯基)乙硫醇
• 英文名称: 3-ethoxy-4-methoxyphenethane thiol
• 英文别名: 2-(3-Ethoxy-4-methoxyphenyl)ethanethiol
• CAS: 396088-09-8
• 化学式: C₁₁H₁₆O₂S
• 分子量: 212.313
• InChiKey: ADRRJYQSGHNFKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  19.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-乙氧基-4-甲氧基苯基)乙硫醇 、 methanesulfonic acid 2-[(2SR,5RS)-2-[4-(benzyloxy)phenyl]-3-(3-carbamoylphenyl)-5-methyl-4-oxo-1,3-thiazolidin-5-yl]ethyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-[(2SR,5RS)-2-[4-(benzyloxy)phenyl]-5-(2-{[2-(3-ethoxy-4-methoxyphenyl)ethyl]thio}ethyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]benzamide
  参考文献：
  名称：

  5-Alkylated thiazolidinones as follicle-stimulating hormone (FSH) receptor agonists

  摘要：

  We prepared analogs of potent thiazolidinone-based follicle-stimulating hormone (FSH) agonists 1, that is, 3 that contained an additional 5-alkyl substituent. This extra substituent was added to reduce synthetic problems that arose during preparation of analogs of 1. These compounds (3) were evaluated in a Chinese hamster ovary (CHO) cell line that expressed recombinant human FSH receptor (FSHR) and a luciferase reporter gene regulated by a cAMP response element (CRE). Selected compounds were also tested on a CHO-cell line that over expressed the FSHR for the ability to induce cAMP production. When the 5-alkyl substituent was a methyl group as in analog 16a, similar FSH activity (i.e., EC50 = 51 nM, 100% efficacy relative to hFSH) to the analogous 5-hydrogen series compound (e.g., 2) was observed; thus, proving that a small 5-alkyl substituent was well tolerated. New derivatives of 3, in which the potentially hydrolytically labile secondary amide function of 1 (-CONH-) was modified to other moieties (e.g., -CH2NH-, -CH2S-, and -CH2O-CONH-), were also prepared and evaluated. These congeners (namely 21, 22, and 24) also displayed good potency in the CRE-luciferase assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.012

文献信息

• 5-Alkylated thiazolidinones as follicle-stimulating hormone (FSH) receptor agonists
  作者：Jay Wrobel、James Jetter、Wenling Kao、John Rogers、Li Di、Jamin Chi、M. Claudia Peréz、Gi-Chung Chen、Emily S. Shen

  DOI：10.1016/j.bmc.2006.04.012

  日期：2006.8

  We prepared analogs of potent thiazolidinone-based follicle-stimulating hormone (FSH) agonists 1, that is, 3 that contained an additional 5-alkyl substituent. This extra substituent was added to reduce synthetic problems that arose during preparation of analogs of 1. These compounds (3) were evaluated in a Chinese hamster ovary (CHO) cell line that expressed recombinant human FSH receptor (FSHR) and a luciferase reporter gene regulated by a cAMP response element (CRE). Selected compounds were also tested on a CHO-cell line that over expressed the FSHR for the ability to induce cAMP production. When the 5-alkyl substituent was a methyl group as in analog 16a, similar FSH activity (i.e., EC50 = 51 nM, 100% efficacy relative to hFSH) to the analogous 5-hydrogen series compound (e.g., 2) was observed; thus, proving that a small 5-alkyl substituent was well tolerated. New derivatives of 3, in which the potentially hydrolytically labile secondary amide function of 1 (-CONH-) was modified to other moieties (e.g., -CH2NH-, -CH2S-, and -CH2O-CONH-), were also prepared and evaluated. These congeners (namely 21, 22, and 24) also displayed good potency in the CRE-luciferase assay. (c) 2006 Elsevier Ltd. All rights reserved.