4-{[(3'-nitrophenyl)carbamoyl]amino}benzenesulfonamide | 178606-71-8

• 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: 4-{[(3'-nitrophenyl)carbamoyl]amino}benzenesulfonamide
• 英文别名: 4-{[(3-nitrophenyl)carbamoyl]amino}benzenesulfonamide；1-(3-nitrophenyl)-3-(4-sulfamoylphenyl)urea
• CAS: 178606-71-8
• 化学式: C₁₃H₁₂N₄O₅S
• 分子量: 336.328
• InChiKey: MTGVDZIMBQRGPD-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C
• 密度：
  1.596±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 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：
  156
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-硝基苯异氢酸酯 、 磺胺 以 乙腈 为溶剂， 反应 24.0h， 以44.3%的产率得到4-{[(3'-nitrophenyl)carbamoyl]amino}benzenesulfonamide
  参考文献：
  名称：

  Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency

  摘要：

  与碳酸酐酶（CA，EC 4.2.1.1）II 复合物结晶的 4-取代脲基苯磺酰胺类化合物对碳酸酐酶（CA，EC 4.2.1.1）II 的抑制活性在 3.3-226 nM 之间。在酶的不同疏水口袋中观察到了抑制剂支架之间的疏水相互作用，从而解释了这些衍生物的不同抑制范围。

  DOI：

  10.1039/c0cc02707c

文献信息

• [EN] NOVEL SULFONAMIDE COMPOUNDS FOR INHIBITION OF METASTATIC TUMOR GROWTH<br/>[FR] NOUVEAUX COMPOSÉS DE SULFONAMIDE DESTINÉS À L'INHIBITION DE LA CROISSANCE TUMORALE MÉTASTATIQUE
  申请人：METASIGNAL THERAPEUTICS INC

  公开号：WO2012021963A1

  公开（公告）日：2012-02-23

  Therapeutic sulfonamide compounds with the formula R-Q-Ar-SO2NH2 are disclosed, wherein R is an aryl, hetaryl, alkyl or cycloalkyl group, Q is the group -L(CH2)n-, wherein n = 0,1 or 2 and L is the group - NHCXNH-, -NHC(S)SNH-, -NHCONHCSNH- or -SO2NH-, X is O or S and Ar is a C6-C10 aromatic or a heteroaromatic group that contains at least one heteroatom of oxygen, nitrogen or sulphur, which compounds selectively inhibit CAIX and CAXII, and which are effective in inhibiting hypoxic tumor growth, suppress metastases, and impair and deplete cancer stem cells in mammals.

  揭示了具有R-Q-Ar-SO2NH2分子式的治疗性磺胺化合物，其中R是芳基、杂环基、烷基或环烷基，Q是基团-L(CH2)n-，其中n = 0、1或2，L是基团-NHCXNH-、-NHC(S)SNH-、-NHCONHCSNH-或-SO2NH-，X是O或S，Ar是含有至少一个氧、氮或硫杂原子的C6-C10芳香或杂芳基团，这些化合物选择性抑制CAIX和CAXII，在抑制缺氧肿瘤生长、抑制转移、损害和消耗哺乳动物中的癌干细胞方面具有有效性。
• Ureido-Substituted Benzenesulfonamides Potently Inhibit Carbonic Anhydrase IX and Show Antimetastatic Activity in a Model of Breast Cancer Metastasis
  作者：Fabio Pacchiano、Fabrizio Carta、Paul C. McDonald、Yuanmei Lou、Daniela Vullo、Andrea Scozzafava、Shoukat Dedhar、Claudiu T. Supuran

  DOI：10.1021/jm101541x

  日期：2011.3.24

  substitution pattern of the urea moiety. Several low nanomolar CA IX/XII inhibitors also showing good selectivity for the transmembrane over the cytosolic isoforms have been discovered. One of them, 4-[(3′-nitrophenyl)carbamoyl]amino}benzenesulfonamide, significantly inhibited the formation of metastases by the highly aggressive 4T1 mammary tumor cells at pharmacologic concentrations of 45 mg/kg, constituting

  制备了一系列脲基取代的苯磺酰胺，它们对抑制几种人类碳酸酐酶（hCAs，EC 4.2.1.1）表现出非常有趣的特性，例如hCAs I和II（胞质同工型）以及hCAs IX和XII（跨膜，肿瘤相关酶）。在该系列的各种成员中，根据脲部分的取代方式，已观察到对所有这些同工型的优异抑制作用。已经发现了几种低纳摩尔浓度的CA IX / XII抑制剂，它们相对于胞质同工型对跨膜也显示出良好的选择性。其中一种是4-[（（3'-硝基苯基）氨基甲酰基]氨基}苯磺酰胺，在药理浓度为45 mg / kg时，可高度抑制高侵袭性4T1乳腺肿瘤细胞转移的形成，
• NOVEL SULFONAMIDE COMPOUNDS FOR INHIBITION OF METASTATIC TUMOR GROWTH
  申请人：METASIGNAL THERAPEUTICS INC.

  公开号：US20130190396A1

  公开（公告）日：2013-07-25

  Therapeutic ureido-sulfonamide compositions having compounds with the formula R-Q-Ar—SO 2 NH 2 are disclosed, which compounds selectively inhibit CAIX and CAXII, and which are effective to inhibit hypoxic tumor growth, suppress metastases, and impair and deplete cancer stem cells in mammals.

  本发明公开了具有以下化学式的化合物的治疗性尿素磺酰胺组合物R-Q-Ar—SO2NH2，这些化合物选择性地抑制CAIX和CAXII，并且有效地抑制哺乳动物中的低氧肿瘤生长，抑制转移并且损害和消耗癌症干细胞。
• Radiosynthesis of three [11C]ureido-substituted benzenesulfonamides as PET probes for carbonic anhydrase IX in tumors
  作者：Chiharu Asakawa、Masanao Ogawa、Katsushi Kumata、Masayuki Fujinaga、Tomoteru Yamasaki、Lin Xie、Joji Yui、Kazunori kawamura、Toshimitsu Fukumura、Ming-Rong Zhang

  DOI：10.1016/j.bmcl.2011.09.102

  日期：2011.12

  Three ureido-substituted benzenesulfonamides 1a-c have been developed as potent inhibitors for carbonic anhydrase IX, which is overexpressed in hypoxic tumors. In this study, we labeled these unsymmetrical ureas 1a-c using [C-11]phosgene ([C-11]COCl2) as a labeling agent with the expectation that [C-11]1a-c could become promising positron tomography probes for imaging carbonic anhydrase IX in tumors. The strategy for radiosynthesis of [C-11]1a-c was to react hydrochloride of anilines 2a-c with [C-11]COCl2 to give isocyanate [C-11]4a-c, followed by a reaction with 4-aminobenzenesulfonamide (3). (C) 2011 Elsevier Ltd. All rights reserved.
• DIANHYDROGALACTITOL TOGETHER WITH RADIATION TO TREAT NON-SMALL-CELL CARCINOMA OF THE LUNG AND GLIOBLASTOMA MULTIFORME
  申请人：Del Mar Pharmaceuticals

  公开号：EP3217970A1

  公开（公告）日：2017-09-20