<<6-methoxy-5-(trifluoromethyl)-1-naphthalenyl>sulfonyl>chloride | 113699-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: <<6-methoxy-5-(trifluoromethyl)-1-naphthalenyl>sulfonyl>chloride
• 英文别名: 5-(trifluoromethyl)-6-methoxy-1-naphthalenesulfonyl chloride；6-methoxy-5-(trifluoromethyl)-1-naphthalenesulfonyl chloride；6-Methoxy-5-(trifluoromethyl)naphthalene-1-sulfonyl chloride
• CAS: 113699-68-6
• 化学式: C₁₂H₈ClF₃O₃S
• 分子量: 324.708
• InChiKey: KVDCTYOFKIXXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <<6-methoxy-5-(trifluoromethyl)-1-naphthalenyl>sulfonyl>chloride 在 吡啶 、 乙酸酐 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 1-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]sulfonyl]-2-thioxo-4-imidazolidinone
  参考文献：
  名称：

  Naphthalenylsulfonyl-hydantoins as aldose reductase inhibitors

  摘要：

  Accumulation of intracellular sorbitol, formed from glucose by aldose reductase, is believed to play an important role in the development of certain chronic complications of diabetes mellitus. Several 1-(naphthalenylsulfonyl)hydantoins inhibit aldose reductase isolated from bovine lens in vitro, and decrease galactitol formation in sciatic nerves of galactosemic rats in vivo. The 5-bromo analogue (entry 12, table I) was found to be the most orally active aldose reductase inhibitor of this series with an ED50 value of 8.1 mg/kg po. The 1-(naphthalenylsulfonyl)-2-thiohydantoin analogues with the exception of entry 11 (table I) which showed good in vivo activity, were either inactive or had only marginal activity.

  DOI：

  10.1016/0223-5234(91)90096-6
• 作为产物：
  描述：

  6-methoxy-5-(trifluoromethyl)-1-naphthylamine 在 盐酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 以50%的产率得到<<6-methoxy-5-(trifluoromethyl)-1-naphthalenyl>sulfonyl>chloride
  参考文献：
  名称：

  Naphthalenylsulfonylimidazolidinediones and their thioxo analogs useful

  摘要：

  本文披露了萘磺酰基咪唑二酮及其硫代类似物以及它们的制备方法。这些化合物是新型的醛糖还原酶抑制剂，可用于治疗或预防糖尿病并发症。

  公开号：

  US04743611A1

文献信息

• Naphthalenylsulfonylimidazolidinediones and their thioxo analogs
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0251784A2

  公开（公告）日：1988-01-07

  The invention comprises naphthalenylsulfonylimidazolidinediones of formula (I) wherein R⁴, R⁵, R⁶ and R⁷ are hydrogen, halogen, trifluoromethyl, methoxy or dimethylamino and X is oxygen or sulfur and the pharmaceutically acceptable salts thereof, and methods for their preparation. The compounds are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications. Pharmaceutical compositions containing the compounds and methods for manufacturing same are also included in the invention.

  本发明包括式 (I) 的萘基磺酰亚胺唑烷二酮，其中 R⁴、R⁵、R⁶ 和 R⁷ 是氢、卤素、三氟甲基、甲氧基或二甲基氨基，X 是氧或硫及其药学上可接受的盐，以及它们的制备方法。 这些化合物是新型醛糖还原酶抑制剂，可用于治疗或预防糖尿病并发症。 本发明还包括含有这些化合物的药物组合物及其生产方法。
• 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.
• MALAMAS, MICHAEL S.;SESTANJ, KAZIMIR
  作者：MALAMAS, MICHAEL S.、SESTANJ, KAZIMIR

  DOI：——

  日期：——
• US4743611A
  申请人：——

  公开号：US4743611A

  公开（公告）日：1988-05-10
• Naphthalenylsulfonylimidazolidinediones and their thioxo analogs useful
  申请人：American Home Products Corp.

  公开号：US04743611A1

  公开（公告）日：1988-05-10

  Disclosed herein are naphthalenylsulfonylimidazolidinediones and their thioxo analogs and methods for their preparation. The compounds are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.

  本文披露了萘磺酰基咪唑二酮及其硫代类似物以及它们的制备方法。这些化合物是新型的醛糖还原酶抑制剂，可用于治疗或预防糖尿病并发症。