3-[3-(3-Methoxy-phenylsulfamoyl)phenyl]-acrylic acid | 412269-24-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[3-(3-Methoxy-phenylsulfamoyl)phenyl]-acrylic acid
• 英文别名: 3-[3-[(3-methoxyphenyl)sulfamoyl]phenyl]prop-2-enoic acid
• CAS: 412269-24-0
• 化学式: C₁₆H₁₅NO₅S
• 分子量: 333.365
• InChiKey: DFADOJIZPFRLNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[3-(3-Methoxy-phenylsulfamoyl)phenyl]-acrylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 生成 3-[3-(3-Methoxy-phenylsulfamoyl)-phenyl]-acryloyl chloride
  参考文献：
  名称：

  Inhibitors of human histone deacetylase with potent activity against the African trypanosome Trypanosoma brucei

  摘要：

  A number of hydroxamic acid derivatives which inhibit human histone deacetylases were investigated for efficacy against cultured bloodstream form Trypanosoma brucei. Three out of the four classes tested displayed significant activity. The majority of compounds blocked parasite growth in the submicromolar range. The most potent was a member of the sulphonepiperazine series with an IC50 of 34 nM. These results identify lead compounds with potential for the development of a novel class of trypanocidal agent. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.072
• 作为产物：
  描述：

  methyl 3-[3-(chlorosulfonyl)phenyl]acrylate 在 sodium hydroxide 作用下， 生成 3-[3-(3-Methoxy-phenylsulfamoyl)phenyl]-acrylic acid
  参考文献：
  名称：

  Inhibitors of human histone deacetylase with potent activity against the African trypanosome Trypanosoma brucei

  摘要：

  A number of hydroxamic acid derivatives which inhibit human histone deacetylases were investigated for efficacy against cultured bloodstream form Trypanosoma brucei. Three out of the four classes tested displayed significant activity. The majority of compounds blocked parasite growth in the submicromolar range. The most potent was a member of the sulphonepiperazine series with an IC50 of 34 nM. These results identify lead compounds with potential for the development of a novel class of trypanocidal agent. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.072

文献信息

• Carbamic acid compounds comprising a sulfonamide linkage as HDAC inhibitors
  申请人：Watkins J. Clare

  公开号：US20050085515A1

  公开（公告）日：2005-04-21

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q 1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S(═O) 2 NR 1 — and —NR 1 S(═O) 2 —; R 1 is a sulfonamido substituent; and, Q 2 is an acid leader group; with the proviso that if J is —S(═O) 2 NR 1 —, then Q 1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  本发明涉及某些活性的碳酰胺酸化合物，其抑制HDAC活性，其化学式为：（I）其中，A是芳基基团；Q1是共价键或芳基领导基团；J是从以下选择的磺酰胺键链：—S（═O）2NR1—和—NR1S（═O）2—；R1是磺酰胺取代基；Q2是酸领导基团；但是，如果J是—S（═O）2NR1—，则Q1是芳基领导基团；以及其药学上可接受的盐、溶剂化物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的制药组合物，以及使用这种化合物和组合物，在体内外抑制HDAC，例如抑制增生状况，如癌症和牛皮癣。
• Carbamic acid compounds comprising a sulfonamide linkage as hdac inhibitors
  申请人：——

  公开号：US20040077726A1

  公开（公告）日：2004-04-22

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S (═O)2NR1— and —NR1S(═O)2—; R1 is a sulfonamido substituent; and, Q2 is an acid leader group; with the proviso that if J is —S(═O)2NR1—, then Q1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  本发明涉及具有以下式子的某些活性碳酸酰化合物，其抑制HDAC活性： （I）A是芳基基团；Q1是共价键或芳基导体基团；J是选择自磺酰胺键的以下链：—S（═O）2NR1—和—NR1S（═O）2—；R1是磺酰胺取代基；Q2是酸导体基团；但是，如果J是—S（═O）2NR1—，则Q1是芳基导体基团；以及其药学上可接受的盐、溶剂化物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这些化合物的制药组合物，以及在体外和体内使用这些化合物和组合物来抑制HDAC，例如抑制增生病症，如癌症和牛皮癣。
• CARBAMIC ACID COMPOUNDS COMPRISING A SULFONAMIDE LINKAGE AS HDAC INHIBITORS
  申请人：Watkins Clare J.

  公开号：US20080161401A1

  公开（公告）日：2008-07-03

  This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q 1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S(═O) 2 NR 1 — and —NR 1 S(═O) 2 —; R 1 is a sulfonamido substituent; and, Q 2 is an acid leader group; with the proviso that if J is —S(═O) 2 NR 1 —, then Q 1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.

  本发明涉及某些活性碳酰胺酸化合物，其抑制HDAC活性，具有以下公式：（I）其中，A是芳基基团；Q1是共价键或芳基引导基团；J是从以下选择的磺酰胺键连接：—S（═O）2NR1—和—NR1S（═O）2—；R1是磺酰胺取代基；Q2是酸引导基团；但是，如果J是—S（═O）2NR1—，则Q1是芳基引导基团；以及其药学上可接受的盐，溶剂化合物，酰胺，酯，醚，化学保护形式和前药。本发明还涉及包含这种化合物的制药组合物，以及在体内外使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。
• Inhibitors of human histone deacetylase with potent activity against the African trypanosome Trypanosoma brucei
  作者：John M. Kelly、Martin C. Taylor、David Horn、Einars Loza、Ivars Kalvinsh、Fredrik Björkling

  DOI：10.1016/j.bmcl.2012.01.072

  日期：2012.3

  A number of hydroxamic acid derivatives which inhibit human histone deacetylases were investigated for efficacy against cultured bloodstream form Trypanosoma brucei. Three out of the four classes tested displayed significant activity. The majority of compounds blocked parasite growth in the submicromolar range. The most potent was a member of the sulphonepiperazine series with an IC50 of 34 nM. These results identify lead compounds with potential for the development of a novel class of trypanocidal agent. (c) 2012 Elsevier Ltd. All rights reserved.