N-(4-formylbenzoyl)benzenesulfonamide | 179056-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-formylbenzoyl)benzenesulfonamide
• 英文别名: N-(benzenesulfonyl)-4-formylbenzamide
• CAS: 179056-90-7
• 化学式: C₁₄H₁₁NO₄S
• 分子量: 289.312
• InChiKey: SVUQRNXGZZWTOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-formylbenzoyl)benzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 N-(4-Cycloheptylaminomethyl-benzoyl)-benzenesulfonamide
  参考文献：
  名称：

  Inhibitors of acyl-CoA: cholesterol O-acyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylylmethyl-N′-arylureas

  摘要：

  A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity, From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10009-8
• 作为产物：
  描述：

  苯磺酰胺 、 对醛基苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到N-(4-formylbenzoyl)benzenesulfonamide
  参考文献：
  名称：

  Inhibitors of acyl-CoA: cholesterol O-acyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylylmethyl-N′-arylureas

  摘要：

  A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity, From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10009-8

文献信息

• Novel peptidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0356595A1

  公开（公告）日：1990-03-07

  This invention relates to analogs of peptidase substrates in which the nitrogen atom of the scissile amide bond of a partial retropeptide analog of the substrate has been replaced by a difluoromethylene moiety. These peptidase substrate analogs provide specific enzyme inhibitors for a variety of proteases, the inhibition of which exert valuable pharmacological activities and therefore have useful physiological consequences in a variety of disease states.

  这项发明涉及肽酶底物的类似物，其中底物的部分反肽类似物的可切割酰胺键的氮原子被二氟甲亚甲基取代。这些肽酶底物类似物提供了各种蛋白酶的特异性酶抑制剂，这些蛋白酶的抑制对多种蛋白酶具有有用的药理活性，因此在多种疾病状态下具有有用的生理后果。
• Aryloxy and arylacyloxy methyl ketones as thiol protease inhibitors
  申请人：SANDOZ LTD.

  公开号：EP0272671A2

  公开（公告）日：1988-06-29

  Thiol protease inhibitors are disclosed having the formula: or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein: n is 0 or 1; m is 0, 1 or 2; X is H or an N-protecting group; each Y is independently an optionally protected α-amino acid residue; R is an optionally protected α-amino acid side chain that is H or CH₃ or that is bonded to the α-carbon atom to which it is attached by a methylene, methine or phenyl radical; and Rʹ is optionally substituted aryl.

  已公开的硫醇蛋白酶抑制剂具有以下式子：或其光学异构体，或其药学上可接受的盐，其中：n为0或1；m为0、1或2；X为H或N-保护基团；每个Y独立地为任选保护的α-氨基酸残基；R为任选保护的α-氨基酸侧链，该侧链为H或CH₃，或通过亚甲基、甲基或苯基与所连接的α-碳原子键合；以及Rʹ为任选取代的芳基。
• HIV protease inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0362002A1

  公开（公告）日：1990-04-04

  This invention relates to analogs of peptidase substrates in which the nitrogen atom of the scissile amide bond of a partial retropeptide analog of the substrate has been replaced by a difluoromethylene moiety. These peptidase substrate analogs provide specific enzyme inhibitors for a variety of proteases, the inhibition of which exert valuable pharmacological activities and therefore have useful physiological consequences in a variety of disease states.

  本发明涉及肽酶底物的类似物，其中底物的部分反肽类似物的巯基酰胺键的氮原子被二氟亚甲基取代。这些肽酶底物类似物为多种蛋白酶提供了特异性酶抑制剂，其抑制作用具有重要的药理活性，因此在多种疾病状态下具有有益的生理作用。
• Novel analogs of peptidase substrates
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0371179A1

  公开（公告）日：1990-06-06

  This invention relates to novel analogs of certain peptidase substrates in which the nitrogen atom of the scissile amide bond has been replaced with difluoro-methyl­ene moiety and in which the carbonyl moiety of its adjacent amide bond has been replaced with a terminal amine function, said novel analogs having the property of inhibiting renin and which are useful in the treatment of hypertension. The novel analogs correspond to the formula

  本发明涉及某些肽酶底物的新型类似物，其中巯基酰胺键的氮原子被二氟亚甲基取代，其相邻酰胺键的羰基被末端胺功能取代，所述新型类似物具有抑制肾素的特性，可用于治疗高血压。这些新型类似物的结构式如下
• Stereoselective reduction of carbonyl compounds
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0963972A2

  公开（公告）日：1999-12-15

  A process for the stereoselective reduction via a Meerwein-Ponndorf-Verley (MPV) reaction, of a carbonyl compound to the corresponding alcohol. A preferred starting carbonyl compound is a ketone compound wherein the carbonyl carbon is prochiral. The starting carbonyl compound is contacted with an MPV mediator such as aluminum isopropoxide. The reaction is conducted under mild conditions, e.g. temperatures of about 50°C or less, for less than four hours, and is capable of producing an excess (about 90% to about 97% or more) of a desired optically active chiral alcohol. The mild reaction conditions preserve the optical orientation of other asymmetric centers in the carbonyl compound starting material.

  一种通过 Meerwein-Ponndorf-Verley (MPV) 反应将羰基化合物立体选择性还原为相应醇的工艺。优选的起始羰基化合物是酮化合物，其中的羰基碳是手性的。起始羰基化合物与 MPV 介质（如异丙醇铝）接触。反应在温和的条件下进行，例如温度约为 50°C 或更低，时间少于四小时，并能生成过量（约 90% 至约 97% 或更多）所需的光学活性手性醇。温和的反应条件可保持羰基化合物起始原料中其他不对称中心的光学取向。