2-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester | 846540-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester
• 英文别名: methyl 2-(trifluoromethylsulfonyloxy)-5,6,7,8-tetrahydronaphthalene-1-carboxylate
• CAS: 846540-87-2
• 化学式: C₁₃H₁₃F₃O₅S
• 分子量: 338.304
• InChiKey: DCIWKZUMXKBPEM-UHFFFAOYSA-N

物化性质

• 沸点：
  431.1±45.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester 在 镍 盐酸 、 palladium diacetate 、 lithium hydroxide 、 氢气 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 为溶剂， 20.0~160.0 ℃ 、413.68 kPa 条件下， 反应 10.5h， 生成 2-{[(2-aminophenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid
  参考文献：
  名称：

  Discovery and Optimization of Anthranilic Acid Sulfonamides as Inhibitors of Methionine Aminopeptidase-2:  A Structural Basis for the Reduction of Albumin Binding

  摘要：

  Methionine aminopeptidase-2 (MetAP2) is a novel target for cancer therapy. As part of an effort to discover orally active reversible inhibitors of MetAP2, a series of anthranilic acid sulfonamides with micromolar affinities for human MetAP2 were identified using affinity selection by mass spectrometry (ASMS) screening. These micromolar hits were rapidly improved to nanomolar leads on the basis of insights from protein crystallography; however, the compounds displayed extensive binding to human serum albumin and had limited activity in cellular assays. Modifications based on structural information on the binding of lead compounds to both MetAP2 and domain III of albumin allowed the identification of compounds with significant improvements in both parameters, which showed good cellular activity in both proliferation and methionine processing assays.

  DOI：

  10.1021/jm0601001
• 作为产物：
  描述：

  2-羟基-1-萘酸甲酯 在 platinum(IV) oxide 吡啶 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， -20.0~20.0 ℃ 、400.01 kPa 条件下， 反应 1.58h， 生成 2-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  [EN] TETRAZOLE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  [FR] COMPOSÉS DE TÉTRAZOLE ET PROCÉDÉS DE PRÉPARATION ET D'UTILISATION DE CEUX-CI

  摘要：

  本文介绍了四唑化合物及其在治疗医学疾病（如肥胖症）中的应用。提供了制备各种四唑化合物的制药组合物和方法。这些化合物被认为对甲硫氨酰基氨肽酶2具有活性。

  公开号：

  WO2012103333A1

文献信息

• [EN] TETRAZOLE COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS DE TÉTRAZOLE ET PROCÉDÉS DE PRÉPARATION ET D'UTILISATION DE CEUX-CI
  申请人：ZAFGEN CORP

  公开号：WO2012103333A1

  公开（公告）日：2012-08-02

  Described herein are tetrazole compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tetrazole compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  本文介绍了四唑化合物及其在治疗医学疾病（如肥胖症）中的应用。提供了制备各种四唑化合物的制药组合物和方法。这些化合物被认为对甲硫氨酰基氨肽酶2具有活性。
• TETRAZOLE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：Dyke Hazel Joan

  公开号：US20130331420A1

  公开（公告）日：2013-12-12

  Described herein are tetrazole compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tetrazole compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  本文描述了四唑化合物及其在治疗医学疾病（如肥胖症）方面的应用。提供了制备各种四唑化合物的制药组合物和方法。这些化合物被认为具有对甲硫氨酰基氨肽酶2的活性。
• Tetrazole compounds and methods of making and using same
  申请人：Dyke Hazel Joan

  公开号：US09321740B2

  公开（公告）日：2016-04-26

  Described herein are tetrazole compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tetrazole compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  本文描述了四唑化合物及其在治疗医学疾病（如肥胖症）中的应用。提供了制备各种四唑化合物的药物组合物和方法。这些化合物被认为具有针对甲硫氨酸氨肽酶2的活性。
• US9321740B2
  申请人：——

  公开号：US9321740B2

  公开（公告）日：2016-04-26
• Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties
  作者：Megumi Kawai、Nwe Y. BaMaung、Steve D. Fidanze、Scott A. Erickson、Jason S. Tedrow、William J. Sanders、Anil Vasudevan、Chang Park、Charles Hutchins、Kenneth M. Comess、Douglas Kalvin、Jieyi Wang、Qian Zhang、Pingping Lou、Lora Tucker-Garcia、Jennifer Bouska、Randy L. Bell、Richard Lesniewski、Jack Henkin、George S. Sheppard

  DOI：10.1016/j.bmcl.2006.03.085

  日期：2006.7

  We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn(2+) as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.