3-(3-nitrophenylsulfonamido)benzoic acid

• 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-(3-nitrophenylsulfonamido)benzoic acid
• 英文别名: 3-((3-Nitrophenyl)sulfonyl)aminobenzoic acid；3-{[(3-Nitrophenyl)sulfonyl]amino}benzoic acid；3-[(3-nitrophenyl)sulfonylamino]benzoic acid
• 化学式: C₁₃H₁₀N₂O₆S
• 分子量: 322.298
• InChiKey: YJCMSQLOXDAOFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-二氯苯胺 、 3-(3-nitrophenylsulfonamido)benzoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以60.8%的产率得到N-(3,4-dichlorophenyl)-3-(3-nitrophenylsulfonamido)benzamide
  参考文献：
  名称：

  Arylsulfonylamino-Benzanilides as Inhibitors of the Apical Sodium-Dependent Bile Salt Transporter (SLC10A2)

  摘要：

  顶端钠依赖性胆盐转运体（ASBT）在维持胆汁酸平衡方面发挥着关键作用。抑制 ASBT 将减少胆汁酸池的大小并降低胆固醇水平。本报告设计并合成了一系列新型芳基磺酰氨基苯甲酰苯胺，作为 ASBT 的潜在抑制剂。其中大多数化合物对 ASBT 的胆汁酸转运活性具有很强的抑制作用。其中，化合物 5g2 抑制 ASBT 活性的 IC50 值为 0.11 μM。这些化合物是潜在的降胆固醇药物。

  DOI：

  10.3390/molecules18066883
• 作为产物：
  描述：

  3-硝基苯磺酰氯 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 17.0h， 生成 3-(3-nitrophenylsulfonamido)benzoic acid
  参考文献：
  名称：

  Arylsulfonylamino-Benzanilides as Inhibitors of the Apical Sodium-Dependent Bile Salt Transporter (SLC10A2)

  摘要：

  顶端钠依赖性胆盐转运体（ASBT）在维持胆汁酸平衡方面发挥着关键作用。抑制 ASBT 将减少胆汁酸池的大小并降低胆固醇水平。本报告设计并合成了一系列新型芳基磺酰氨基苯甲酰苯胺，作为 ASBT 的潜在抑制剂。其中大多数化合物对 ASBT 的胆汁酸转运活性具有很强的抑制作用。其中，化合物 5g2 抑制 ASBT 活性的 IC50 值为 0.11 μM。这些化合物是潜在的降胆固醇药物。

  DOI：

  10.3390/molecules18066883

文献信息

• Arylsulfonylaminobenzene derivatives and the use thereof as factor Xa
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US05741819A1

  公开（公告）日：1998-04-21

  The present invention is directed to non-peptidic factor Xa inhibitors which are useful for the treatment of arterial and venous thrombotic occlusive disorders, inflammation, cancer, and neurodegenerative diseases. The factor Xa inhibitors provide compounds of structure: ##STR1## or pharmaceutically acceptable salts thereof; wherein R.sup.1 is alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl; R.sup.2 is one of hydrogen, alkyl, cycloalkyl or aryl; R.sup.3 is one of hydrogen, hydroxy or alkoxy; R.sup.4 is one of --NH.sub.2, phenyl or pyridyl, wherein said phenyl and said pyridyl are optionally substituted with one or two of halogen, hydroxy, hydroxyalkyl, alkoxy, amino, monoalkylamino, dialkylamino, aminoalkyl, monoalkylaminoalkyl and/or dialkylaminoalkyl; X is one of --CH.sub.2 -- or --C(O)--; and n is from zero to eleven; provided that when R.sup.4 is --NH.sub.2, then R.sup.3 is hydrogen and n is other than zero; and also provided that when R.sup.3 is hydroxy or alkoxy, then R.sup.4 is other than --NH.sub.2, and n is other than zero.

  本发明涉及用于治疗动脉和静脉血栓性闭塞性疾病、炎症、癌症和神经退行性疾病的非肽因子Xa抑制剂。因子Xa抑制剂提供结构化合物：##STR1##或其药学上可接受的盐；其中R.sup.1是烷基、取代烷基、环烷基、芳基、取代芳基、杂环芳基或取代杂环芳基；R.sup.2是氢、烷基、环烷基或芳基中的一种；R.sup.3是氢、羟基或烷氧基中的一种；R.sup.4是--NH.sub.2、苯基或吡啶基中的一种，其中所述苯基和所述吡啶基可以选择地取代为卤素、羟基、羟基烷基、烷氧基、氨基、单烷基氨基、二烷基氨基、氨基烷基、单烷基氨基烷基和/或二烷基氨基烷基中的一种或两种；X是--CH.sub.2--或--C(O)--中的一种；n为零到十一；但是当R.sup.4为--NH.sub.2时，R.sup.3为氢且n不为零；同时当R.sup.3为羟基或烷氧基时，R.sup.4不为--NH.sub.2，且n不为零。
• ——
  作者：T. P. Kustova、L. V. Kuritsyn、L. N. Khripkova

  DOI：10.1023/a:1012351722560

  日期：——

  The concentrations of the uncharged and anionic forms of m- and p-aminobenzoic acids participating in arylsulfonation of the acids with m- and p-nitrobenzenesulfonyl chlorides in the system water-2-propanol at 298 K at various water contents and pHs were estimated. The resulting. data were used to estimate the rate constants for the reactions of the above forms with nitrobenzenesulfonyl chlorides, based on experimental kinetic data.
• Virtual Screening Identification of Nonfolate Compounds, Including a CNS Drug, as Antiparasitic Agents Inhibiting Pteridine Reductase
  作者：Stefania Ferrari、Federica Morandi、Domantas Motiejunas、Erika Nerini、Stefan Henrich、Rosaria Luciani、Alberto Venturelli、Sandra Lazzari、Samuele Calò、Shreedhara Gupta、Veronique Hannaert、Paul A. M. Michels、Rebecca C. Wade、M. Paola Costi

  DOI：10.1021/jm1010572

  日期：2011.1.13

  Folate analogue inhibitors of Leishmania major pteridine reductase (PTR1) are potential antiparasitic drug candidates for combined therapy with dihydrofolate reductase (DHFR) inhibitors To identify new molecules with specificity for PTR1, we carried out a virtual screening of the Available Chemicals Directory (ACD) database to select compounds that could interact with L major PTR1 but not with human DHFR Through two rounds of drug discovery, we successfully identified eighteen drug-like molecule, with low micromolar affinities and high in vitro specificity profiles Their efficacy against Leishmania species was studied in cultured cells of the promastigote stage, using the compounds both alone and in combination with 1 (pyrimethamine, 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine) Six compounds showed efficacy only in combination In toxicity tests against human fibroblasts, several compounds showed low toxicity One compound, 5c (riluzole, 6-(trifluoromethoxy)-1,3-benzothiazol-2-ylamine,), a known drug approved for CNS pathologies, was active in combination and is suitable for early preclinical evaluation of its potential for label extension as a PTR1 inhibitor and antiparasitic drug candidate
• ARYLSULFONYLAMINOBENZENE DERIVATIVES AND THE USE THEREOF AS FACTOR Xa INHIBITORS
  申请人：3-DIMENSIONAL PHARMACEUTICALS, INC.

  公开号：EP0831800A1

  公开（公告）日：1998-04-01
• EP0831800A4
  申请人：——

  公开号：EP0831800A4

  公开（公告）日：1999-03-10