乙基5-乙基-2-异硫氰酸基-3-噻吩羧酸酯 | 109343-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 乙基5-乙基-2-异硫氰酸基-3-噻吩羧酸酯
• 英文名称: 5-Ethyl-2-isothiocyanato-thiophene-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-ethyl-2-isothiocyanatothiophene-3-carboxylate
• CAS: 109343-21-7
• 化学式: C₁₀H₁₁NO₂S₂
• 分子量: 241.335
• InChiKey: BNICADDGDCDEQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  乙基5-乙基-2-异硫氰酸基-3-噻吩羧酸酯 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-Amino-6-ethyl-2-{3-[4-(2-methoxy-phenyl)-piperazin-1-yl]-propylsulfanyl}-3H-thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  High affinity and selectivity of [[(arylpiperazinyl)alkyl]thio]thieno[2,3-d]pyrimidinone derivatives for the 5-HT1A receptor.Synthesis and structure–affinity relationships

  摘要：

  In this work we report the affinity of new thienopyrimidinones for 5-HT(1A)Rs and the selectivity versus alpha(1)ARs. The 3-amino-2-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]thio]-6-ethyl-thieno[2,3-d]pyrimidin-4(3H)-one 27 is the most potent and selective (Ki 0.19 nM, selectivity 115). Compound 31 with the N4 piperazine orthonitrophenyl nucleus instead of the orthomethoxyphenyl also shows a good affinity and selectivity (Ki 1.46 nM, selectivity 84). The results of derivatives 28, 29 and 30 (Ki 3.28, 12.59 and 4.38 nM; selectivity 24, 4 and 5, respectively), which have, respectively, an ethyl, an allyl and an acetylamino group instead of an N3 amino group, indicate the importance of this last group for the interaction with 5-HT1AR. Comparison of the results for the superior homologue 53 (Ki 3.72 nM, selectivity 51) and the inferior homologue 52 (5-HT1A Ki 1 499 nM, alpha(1)A Ki NA) of 2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-6,7-dimethyl-8H-[1,3,4]thiadiazolo[3,2-a]thieno[2,3-d]pyrimidin-8-one 57 (Ki 23 nM, selectivity 5) shows how important the length of the chain binding the two heterocyclic systems is in the interaction with 5-HT(1A)Rs and alpha(1)ARs. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00175-6
• 作为产物：
  描述：

  净司他丁 、 硫光气 在 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以79%的产率得到乙基5-乙基-2-异硫氰酸基-3-噻吩羧酸酯
  参考文献：
  名称：

  Bohm; Muller; Pech, Pharmazie, 1990, vol. 45, # 11, p. 827 - 829

  摘要：

  DOI：

文献信息

• High affinity and selectivity of [[(arylpiperazinyl)alkyl]thio]thieno[2,3-d]pyrimidinone derivatives for the 5-HT1A receptor.Synthesis and structure–affinity relationships
  作者：Maria Modica、Maria Santagati、Filippo Russo、Carlo Selvaggini、Alfredo Cagnotto、Tiziana Mennini

  DOI：10.1016/s0223-5234(00)00175-6

  日期：2000.8

  In this work we report the affinity of new thienopyrimidinones for 5-HT(1A)Rs and the selectivity versus alpha(1)ARs. The 3-amino-2-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]thio]-6-ethyl-thieno[2,3-d]pyrimidin-4(3H)-one 27 is the most potent and selective (Ki 0.19 nM, selectivity 115). Compound 31 with the N4 piperazine orthonitrophenyl nucleus instead of the orthomethoxyphenyl also shows a good affinity and selectivity (Ki 1.46 nM, selectivity 84). The results of derivatives 28, 29 and 30 (Ki 3.28, 12.59 and 4.38 nM; selectivity 24, 4 and 5, respectively), which have, respectively, an ethyl, an allyl and an acetylamino group instead of an N3 amino group, indicate the importance of this last group for the interaction with 5-HT1AR. Comparison of the results for the superior homologue 53 (Ki 3.72 nM, selectivity 51) and the inferior homologue 52 (5-HT1A Ki 1 499 nM, alpha(1)A Ki NA) of 2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-6,7-dimethyl-8H-[1,3,4]thiadiazolo[3,2-a]thieno[2,3-d]pyrimidin-8-one 57 (Ki 23 nM, selectivity 5) shows how important the length of the chain binding the two heterocyclic systems is in the interaction with 5-HT(1A)Rs and alpha(1)ARs. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Bohm; Muller; Pech, Pharmazie, 1990, vol. 45, # 11, p. 827 - 829
  作者：Bohm、Muller、Pech

  DOI：——

  日期：——