(R)-2-[4-(2,3-Dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenoxy]-propionic acid methyl ester | 264254-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (R)-2-[4-(2,3-Dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenoxy]-propionic acid methyl ester
• 英文别名: methyl (2R)-2-[4-(2,3-dimethyl-[1]benzothiolo[3,2-f][1]benzofuran-4-yl)-2,6-diiodophenoxy]propanoate
• CAS: 264254-52-6
• 化学式: C₂₆H₂₀I₂O₄S
• 分子量: 682.317
• InChiKey: TWEXHAVNQPTLME-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.23
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[4-(2,3-Dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenoxy]-propionic acid methyl ester 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 32.0h， 以95%的产率得到(R)-2-[4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenoxy]-propionic acid
  参考文献：
  名称：

  Synthesis and PTP1B Inhibition of Novel 4-Aryl-1-Oxa-9-Thiacyclopenta[b]fluorenes

  摘要：

  Novel 4-aryl-1-oxa-9-thiacyclopenta[b]fluorenes were designed, synthesized, and evaluated as inhibitors of the protein tyrosine phosphatase, PTP1B. Compounds 3 (IC50 = 284 nM) and 4 (IC50 = 74 nM), showed nanomolar potency against PTP1B (TRDI(P)YETD(P)Y(P)YRK as substrate). Compound 4 also lowered insulin in the diabetic ob/ob mouse at a dose of 10 mg/kg/day, po. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00278-x
• 作为产物：
  描述：

  4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-phenol 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 苯 为溶剂， 反应 18.0h， 生成 (R)-2-[4-(2,3-Dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenoxy]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and PTP1B Inhibition of Novel 4-Aryl-1-Oxa-9-Thiacyclopenta[b]fluorenes

  摘要：

  Novel 4-aryl-1-oxa-9-thiacyclopenta[b]fluorenes were designed, synthesized, and evaluated as inhibitors of the protein tyrosine phosphatase, PTP1B. Compounds 3 (IC50 = 284 nM) and 4 (IC50 = 74 nM), showed nanomolar potency against PTP1B (TRDI(P)YETD(P)Y(P)YRK as substrate). Compound 4 also lowered insulin in the diabetic ob/ob mouse at a dose of 10 mg/kg/day, po. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00278-x