4-sulfamoyl-1,1'-biphenyl-4'-carboxylic acid | 199678-14-3

• 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: 4-sulfamoyl-1,1'-biphenyl-4'-carboxylic acid
• 英文别名: 4’-sulfamoyl[1,1’-biphenyl]-4-carboxylic acid；4-(4-Aminosulfonylphenyl)benzoic acid；4-(4-sulfamoylphenyl)benzoic acid
• CAS: 199678-14-3
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: WVXCHHVMFRGCEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-sulfamoyl-1,1'-biphenyl-4'-carboxylic acid 在 盐酸 、 氨 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(E)-3-(5-carbamimidoyl-2-hydroxyphenyl)prop-2-enyl]-4-(4-sulfamoylphenyl)benzamide
  参考文献：
  名称：

  Amido-(propyl and allyl)-hydroxybenzamidines: development of achiral inhibitors of factor Xa

  摘要：

  The design, synthesis and SAR of amido-(propyl and allyl)-hydroxybenzamidine coagulation factor Xa inhibitors is described. These achiral inhibitors are selective for fXa vis a vis structurally related serine proteases and are readily prepared in 6-7 linear steps. The most potent member 9j (fXa K-i = 0.75 nM) is selective (>1000-fold) and an effective anticoagulant in mammalian plasma. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00673-3
• 作为产物：
  描述：

  methyl 4-sulfamoyl-1,1'-biphenyl-4'-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 氘代四氢呋喃 、 水 为溶剂， 反应 12.0h， 以95%的产率得到4-sulfamoyl-1,1'-biphenyl-4'-carboxylic acid
  参考文献：
  名称：

  Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors

  摘要：

  New 1,1'-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound. The sulfonamides 1-21 inhibited all the isoforms, with K-i values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallography and molecular modeling studies on the adducts that compound 20, the most potent hCA XIV inhibitor of the series (K-i, = 0.26 nM), formed with the five hCAs, provided insight into the molecular determinants responsible for the high affinity of this molecule toward the target enzymes. The results pave the way to the development of 1.1'-biphenylsulfonamides as a new class of highy potent hCA XIV inhibitors.

  DOI：

  10.1021/acs.jmedchem.5b01144

文献信息

• 1-aroyl-piperidinyl benzamidines
  申请人：——

  公开号：US20020045613A1

  公开（公告）日：2002-04-18

  This invention relates to compounds of formula 1 which inhibit Factor Xa or tryptase, to pharmaceutical compositions containing the compounds, and to the use of the compounds for the treatment of patients suffering from conditions which can be ameliorated by the administration of an inhibitor of Factor Xa or tryptase.

  该发明涉及一种公式1的化合物，其能够抑制Xa因子或胰蛋白酶，以及含有这些化合物的药物组合物，以及利用这些化合物治疗患有可以通过给予Xa因子或胰蛋白酶抑制剂而得到改善的病患的方法。
• 1-Aroyl-piperidinyl benzamidines
  申请人：AVENTIS PHARMACEUTICALS INC

  公开号：US20040220171A1

  公开（公告）日：2004-11-04

  This invention relates to compounds of formula 1 which inhibit Factor Xa or tryptase, to pharmaceutical compositions containing the compounds, and to the use of the compounds for the treatment of patients suffering from conditions which can be ameliorated by the administration of an inhibitor of Factor Xa or tryptase.

  本发明涉及式1化合物，其抑制因子Xa或胰蛋白酶，以及含有该化合物的药物组合物，以及使用该化合物治疗患有可通过给予因子Xa或胰蛋白酶抑制剂治疗的疾病的患者的用途。
• A prodrug design for improved oral absorption and reduced hepatic interaction
  作者：Gulzar Ahmed、Walter Elger、Frederick Meece、Hareesh B. Nair、Birgitt Schneider、Ralf Wyrwa、Klaus Nickisch

  DOI：10.1016/j.bmc.2017.08.027

  日期：2017.10

  A series of estradiol-17-beta esters of N-(p-sulfomylbenzamide)-amino acids were prepared and evaluated for systemic and hepatic estrogenic activity after oral administration in ovariectomized rats. The alkyl substitution at nitrogen of amino acids such as proline or N-methyl-alanine produced compounds that exhibit potent oral activity. The proline analog (EC508) was further evaluated along with 17 beta-estradiol (E2) and ethinyl-estradiol (EE) and compared their effects on the uterus, angiotensin and HDL-cholesterol after oral administration to ovariectomized female rats. Orally administered EC508 produced systemic estrogenic activity 10 times greater than EE and a 100 times higher activity than E2 with no influence on levels of angiotensin and HDL-cholesterol, whereas EE and E2 reduced the HDL-cholesterol and increased the angiotensine plasma levels. EC508 might offer significant advantages in indications like fertility control and HRT based on its high oral bioavailability and lack of hepatic estrogenicity. (C) 2017 Elsevier Ltd. All rights reserved.
• TETRAHYDROISOQUINOLINE DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0917530A1

  公开（公告）日：1999-05-26
• 1-AROYL-PIPERIDINYL BENZAMIDINES
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1278732A1

  公开（公告）日：2003-01-29