Carbonic acid 6-(2,4-dioxo-thiazolidin-5-ylsulfanyl)-3-ethoxycarbonyloxy-naphthalen-2-yl ester ethyl ester | 125518-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Carbonic acid 6-(2,4-dioxo-thiazolidin-5-ylsulfanyl)-3-ethoxycarbonyloxy-naphthalen-2-yl ester ethyl ester
• 英文别名: [6-[(2,4-Dioxo-1,3-thiazolidin-5-yl)sulfanyl]-3-ethoxycarbonyloxynaphthalen-2-yl] ethyl carbonate
• CAS: 125518-75-4
• 化学式: C₁₉H₁₇NO₈S₂
• 分子量: 451.478
• InChiKey: URRVEKHLDWHCKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Carbonic acid 6-(2,4-dioxo-thiazolidin-5-ylsulfanyl)-3-ethoxycarbonyloxy-naphthalen-2-yl ester ethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以40%的产率得到5-(6,7-Dihydroxy-naphthalen-2-ylsulfanyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones

  摘要：

  A series of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones were synthesized and evaluated for antihyperglycemic activity in an insulin-resistant, genetically diabetic db/db mouse model of non-insulin-dependent diabetes mellitus (NIDDM). The sulfones could be synthesized by a novel, selective C-5 sulfonylation of dilithio-2,4-thiazolidinedione with appropriate sulfonyl chlorides. Within this series, naphthalene was found to be superior to other groups for eliciting antihyperglycemic activity, including the p-alkoxyphenyl group found in ciglitazone, a prototypical agent for this activity. Attachment of the 5-sulfonyl-2,4-thiazolidinedione moiety to the 2-naphthalene position led to optimum activity. Other linkers between the naphthalene and 2,4-thiazolidinedione rings, such as thio, methylene, oxy, and sulfinyl led to decreased antihyperglycemic activity. The best analogue, 5-(2-naphthalenylsulfonyl)-2,4-thiazolidinedione (AY-31,637) was equipotent to ciglitazone in two animal models of NIDDM.

  DOI：

  10.1021/jm00167a022
• 作为产物：
  描述：

  5-溴噻唑烷-2,4-二酮 、 6,7-bis<(ethoxycarbonyl)oxy>-2-mercaptonaphthalene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到Carbonic acid 6-(2,4-dioxo-thiazolidin-5-ylsulfanyl)-3-ethoxycarbonyloxy-naphthalen-2-yl ester ethyl ester
  参考文献：
  名称：

  Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones

  摘要：

  A series of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones were synthesized and evaluated for antihyperglycemic activity in an insulin-resistant, genetically diabetic db/db mouse model of non-insulin-dependent diabetes mellitus (NIDDM). The sulfones could be synthesized by a novel, selective C-5 sulfonylation of dilithio-2,4-thiazolidinedione with appropriate sulfonyl chlorides. Within this series, naphthalene was found to be superior to other groups for eliciting antihyperglycemic activity, including the p-alkoxyphenyl group found in ciglitazone, a prototypical agent for this activity. Attachment of the 5-sulfonyl-2,4-thiazolidinedione moiety to the 2-naphthalene position led to optimum activity. Other linkers between the naphthalene and 2,4-thiazolidinedione rings, such as thio, methylene, oxy, and sulfinyl led to decreased antihyperglycemic activity. The best analogue, 5-(2-naphthalenylsulfonyl)-2,4-thiazolidinedione (AY-31,637) was equipotent to ciglitazone in two animal models of NIDDM.

  DOI：

  10.1021/jm00167a022

文献信息

• Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones
  作者：Arie Zask、Ivo Jirkovsky、James W. Nowicki、Michael L. McCaleb

  DOI：10.1021/jm00167a022

  日期：1990.5

  A series of 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones were synthesized and evaluated for antihyperglycemic activity in an insulin-resistant, genetically diabetic db/db mouse model of non-insulin-dependent diabetes mellitus (NIDDM). The sulfones could be synthesized by a novel, selective C-5 sulfonylation of dilithio-2,4-thiazolidinedione with appropriate sulfonyl chlorides. Within this series, naphthalene was found to be superior to other groups for eliciting antihyperglycemic activity, including the p-alkoxyphenyl group found in ciglitazone, a prototypical agent for this activity. Attachment of the 5-sulfonyl-2,4-thiazolidinedione moiety to the 2-naphthalene position led to optimum activity. Other linkers between the naphthalene and 2,4-thiazolidinedione rings, such as thio, methylene, oxy, and sulfinyl led to decreased antihyperglycemic activity. The best analogue, 5-(2-naphthalenylsulfonyl)-2,4-thiazolidinedione (AY-31,637) was equipotent to ciglitazone in two animal models of NIDDM.