4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-phenol | 264254-48-0

• 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: 4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-phenol
• 英文别名: 4-(2,3-Dimethyl-[1]benzothiolo[3,2-f][1]benzofuran-4-yl)phenol
• CAS: 264254-48-0
• 化学式: C₂₂H₁₆O₂S
• 分子量: 344.434
• InChiKey: WXZWKYPVOYSSSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-phenol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以54%的产率得到4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenol
  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)-phenyl methyl ether 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以94%的产率得到4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-phenol
  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

文献信息

• 4-aryl-1-oxa-9-thia-cyclopenta (b) fluorenes
  申请人：American Home Products Corporation

  公开号：US20010020037A1

  公开（公告）日：2001-09-06

  This invention provides compounds of Formula I having the structure 1 wherein B and D are each, independently, hydrogen, halogen, —CN, alkyl of 1-6 carbon atoms, aryl, or aralkyl of 6-12 carbon atoms; R 1 is hydrogen, alkyl of 1-6 carbon atoms, —CH(R 2 )W, —C(CH 3 ) 2 CO 2 R 3 , 5-thiazolidine-2,4-dione, —CH(R 4 )CH 2 CO 2 R 3 , —COR 3 , or —PO 3 (R 3 ) 2 ; R 2 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, aryl, —CH 2 (1H-imidazol-4-yl), —CH 2 (3-1H-indolyl), —CH 2 CH 2 (1,3-dioxo-1,3-dihydro-isoindol-2-yl), —CH 2 CH 2 (1-oxo-1,3-dihydro-isoindol-2-yl), or —CH 2 (3-pyridyl); W is —CO 2 R 3 , —CONH 2 , —CONHOH, —CN, CONH(CH 2 ) 2 CN, 5-tetrazole, or —PO 3 (R 3 ) 2 ; R 3 is hydrogen, alkyl of 1-6 carbon atoms, or, aryl; R 4 is hydrogen or alkyl of 1-6 carbon atoms; or a pharmaceutically acceptable salt thereof, which are useful in treating, metabolic disorders related to insulin resistance or hyperglycemia.

  本发明提供了式I的化合物，其结构为1其中B和D各自独立地为氢、卤素、—CN、1-6个碳原子的烷基、芳基或6-12个碳原子的芳基烷基；R1为氢、1-6个碳原子的烷基、—CH(R2)W、—C(CH3)2CO2R3、5-噻唑烷-2,4-二酮、—CH(R4)CH2CO2R3、—COR3或—PO3(R3)2；R2为氢、1-6个碳原子的烷基、6-12个碳原子的芳基烷基、芳基、—CH2(1H-咪唑-4-基)、—CH2(3-1H-吲哚基)、—CH2CH2(1,3-二氢-2-氮杂-异吲哚-2-基)、—CH2CH2(1-氧代-1,3-二氢-异吲哚-2-基)或—CH2(3-吡啶基)；W为—CO2R3、—CONH2、—CONHOH、—CN、CONH(CH2)2CN、5-四唑或—PO3(R3)2；R3为氢、1-6个碳原子的烷基或芳基；R4为氢或1-6个碳原子的烷基；或其药学上可接受的盐，用于治疗与胰岛素抵抗或高血糖有关的代谢紊乱。
• US6057316A
  申请人：——

  公开号：US6057316A

  公开（公告）日：2000-05-02
• US6281238B1
  申请人：——

  公开号：US6281238B1

  公开（公告）日：2001-08-28
• US6340676B2
  申请人：——

  公开号：US6340676B2

  公开（公告）日：2002-01-22
• Synthesis and PTP1B Inhibition of Novel 4-Aryl-1-Oxa-9-Thiacyclopenta[b]fluorenes
  作者：Jay Wrobel、Zenan Li、Janet Sredy、Diane R Sawicki、Laura Seestaller、Donald Sullivan

  DOI：10.1016/s0960-894x(00)00278-x

  日期：2000.7

  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.