3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxyacetaldehyde | 197960-30-8

• 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: 3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxyacetaldehyde
• 英文别名: [3-methyl-5-(2-oxoethoxy)phenyl] 2-methoxybenzenesulfonate
• CAS: 197960-30-8
• 化学式: C₁₆H₁₆O₆S
• 分子量: 336.365
• InChiKey: JCLNPKOSYFQDEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氨基胍硝酸盐 、 3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxyacetaldehyde 生成 3-[((2E)-2-{[(E)-amino(imino)methyl]hydrazono}ethyl)oxy]-5-methylphenyl 2-methoxybenzenesulfonate
  参考文献：
  名称：

  Amidinohydrazones as guanidine bioisosteres: application to a new class of potent, selective and orally bioavailable, non-amide-based small-molecule thrombin inhibitors

  摘要：

  We describe a new class of potent, non-amide-based small molecule thrombin inhibitors in which an amidinohydrazone is used as a guanidine bioisostere on a non-peptide scaffold. Compound 4 exhibits nM inhibition of thrombin, is selective for thrombin, and shows 60 and 23% bioavailability in rabbits and dogs, respectively. Crystallographic analysis of 4 bound to thrombin confirmed the amindinohydrazone binding mode. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00632-0
• 作为产物：
  描述：

  3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenol 在 palladium on activated charcoal pyridine-SO3 complex 、 三丁基膦 、 氢气 、 二甲基亚砜 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxyacetaldehyde
  参考文献：
  名称：

  Amidinohydrazones as guanidine bioisosteres: application to a new class of potent, selective and orally bioavailable, non-amide-based small-molecule thrombin inhibitors

  摘要：

  We describe a new class of potent, non-amide-based small molecule thrombin inhibitors in which an amidinohydrazone is used as a guanidine bioisostere on a non-peptide scaffold. Compound 4 exhibits nM inhibition of thrombin, is selective for thrombin, and shows 60 and 23% bioavailability in rabbits and dogs, respectively. Crystallographic analysis of 4 bound to thrombin confirmed the amindinohydrazone binding mode. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00632-0

文献信息

• Amidinohydrazones as protease inhibitors
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US05891909A1

  公开（公告）日：1999-04-06

  Amidino and benzamidino compounds, including compounds of the formula: ##STR1## wherein R.sup.1 -R.sup.4, R.sup.6 -R.sup.9, Y, Z, n and m are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin are described. Also described are methods for preparing the compounds of Formula I.

  阿米地诺和苯基氨基甲酰胺化合物，包括以下式的化合物：##STR1## 其中R.sup.1 -R.sup.4，R.sup.6 -R.sup.9，Y，Z，n和m在规范中列出，以及其水合物，溶剂合物或药用可接受盐，能抑制蛋白酶酶，如凝血酶。还描述了制备式I化合物的方法。
• [EN] AMIDINOHYDRAZONES AS PROTEASE INHIBITORS<br/>[FR] AMIDINOHYDRAZONES UTILISES EN QUALITE D'INHIBITEURS DE PROTEASE
  申请人：3-DIMENSIONAL PHARMACEUTICALS, INC.

  公开号：WO1997036580A1

  公开（公告）日：1997-10-09

  (EN) Amidino and benzamidino compounds, including compounds of formula (I), wherein R1-R4, R6-R9, Y, Z, n and m are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin are described. Also described are methods for preparing the compounds of formula (I).(FR) Cette invention concerne des composés amidino et benzamidino, et notamment des composés correspondant à la formule (I) où R1-R4, R6-R9, Y, Z, n et m sont tels que définis dans la description. Cette invention concerne également des hydrates, des solvates ou des sels de ces composés acceptables sur le plan pharmaceutique, lesquels permettent d'inhiber des enzymes protéolytiques telles que la thrombine. Cette invention concerne également des procédés de préparation des composés correspondant à la formule (I).

  该专利描述了一类抑制蛋白酶酶活性的化合物，包括公式（I）中所述的R1-R4、R6-R9、Y、Z、n和m，以及其水合物、溶剂化合物或药学上可接受的盐。同时，该专利还描述了制备公式（I）中所述化合物的方法。
• AMIDINOHYDRAZONES AS PROTEASE INHIBITORS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0906091B1

  公开（公告）日：2006-10-04
• EP0906091A4
  申请人：——

  公开号：EP0906091A4

  公开（公告）日：2004-07-21
• US5891909A
  申请人：——

  公开号：US5891909A

  公开（公告）日：1999-04-06