N⁴-(Benzoyl)sulfanilyl chloride | 67377-44-0

• 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: N⁴-(Benzoyl)sulfanilyl chloride
• 英文别名: 4-benzamidobenzenesulfonyl chloride；4-(benzoylamino)benzenesulfonyl chloride；N-benzoyl-sulfaniloyl chloride；N-Benzoyl-sulfanilsaeure-chlorid；4-Benzamino-benzol-sulfonsaeure-(1)-chlorid；4-Benzamidobenzene-1-sulfonyl chloride
• CAS: 67377-44-0
• 化学式: C₁₃H₁₀ClNO₃S
• mdl: MFCD09814767
• 分子量: 295.746
• InChiKey: LKICQRVDNWUUSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N⁴-(Benzoyl)sulfanilyl chloride 在 sodium hydroxide 、 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 methyl-BAPSG
  参考文献：
  名称：

  N- [4-（苯甲酰基氨基）苯基磺酰基]甘氨酸（一种新型的醛糖还原酶抑制剂）的前药在体外的水解，通透性和眼吸收。

  摘要：

  为了增强N- [4-（苯甲酰基氨基）苯基磺酰基]甘氨酸（BAPSG）的眼吸收能力，合成了两种酯（甲基和异丙基）前药并评估了它们在各种缓冲液（pH 1-9）中的稳定性，在兔眼中的水解组织（角膜，结膜，虹膜睫状体，晶状体，房水和玻璃体液），跨角膜和结膜的运输以及局部给药后的体内摄取。在1-9的pH范围内，甲基丙烯酸酯的降解速率常数为5.67至218.9 x 10（-3）h（-1），而甲基丙烯酸酯的降解速率常数为3.14至4.45 x 10（-3）h（-1）用于异丙酯。在所有pH条件下，与甲基酯相比，异丙酯都更稳定。pH 7.4时缓冲液浓度的变化不会影响前药的稳定性。前药在组织匀浆中迅速水解，甲酯的水解速率常数范围为1.98至7.2x 10（-3）min（-1），异丙酯的水解速率常数范围为3.32至6.53 x 10（-3）min（-1）。甲酯在角膜和结膜中的体外渗透性小于母体药物。即使在4小时

  DOI：

  10.1211/0022357001774877
• 作为产物：
  描述：

  对氨基苯磺酸 在 草酰氯 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N⁴-(Benzoyl)sulfanilyl chloride
  参考文献：
  名称：

  Design, synthesis and biological evaluation of suramin-derived dual antagonists of the proinflammatory G protein-coupled receptors P2Y2 and GPR17

  摘要：

  Dual- or multi-target drugs are particularly promising for the treatment of complex diseases such as (neuro)inflammatory disorders. In the present study, we identified dual antagonists for two related proinflammatory G protein-coupled receptors (GPCRs), the purinergic receptor P2Y(2) receptor, and the orphan receptor GPR17. Based on the lead compound suramin small molecules were designed, synthesized, and modified, including benzenesulfonate, benzenesulfonamide, dibenzamide and diphenylurea derivatives. Structure-activity relationship studies identified 3-nitrophenyl 4-benzamidobenzenesulfonic acid derivatives as dual P2Y(2)R/GPR17 antagonists. In particular, 3-nitrophenyl 4-(4-chlorobenzamido) benzenesulfonate (14l, IC50 3.01 mu M at P2Y(2)R, and 3.37 mu M at GPR17) and 3-nitrophenyl-4-(2-chlorobenzamido)benzenesulfonate (14m, IC50 3.17 mu M at P2Y(2)R, and 1.67 mu M at GPR17) exhibited dual antagonistic activity. Compound 14l was shown to act as an allosteric antagonist at both receptors. In addition, GPR17-selective antagonists were identified( )including 3-nitrophenyl 4-benzamidobenzenesulfonate (14a, IC50 3.20 mu M) and 3-nitrophenyl 4-(3-(trifluoromethyl)benzamido) benzenesulfonate (14f, IC50 3.88 mu M). The developed antagonists were selective versus other closely related P2Y receptors. They were found to possess high chemical and metabolic stability in human liver microsomes and therefore present good starting points for developing potent multi-target drugs with potential applications in inflammatory diseases. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111789

文献信息

• N- and 2-substituted N-(phenylsulfonyl)glycines as inhibitors of rat lens aldose reductase
  作者：Jack DeRuiter、Ronald F. Borne、Charles A. Mayfield

  DOI：10.1021/jm00121a027

  日期：1989.1

  A variety of N-(phenylsulfonyl)-N-phenylglycines 5, N-(phenylsulfonyl)-2-phenylglycines 6, and N-(phenylsulfonyl)anthranilic acids 7 were prepared as analogues of the N-(phenylsulfonyl)glycine 1 aldose reductase inhibitors. In the rat lens assay, several derivatives of 5 display greater inhibitory activity than the corresponding glycines 1, suggesting that N-phenyl substitution enhances affinity for

  制备了多种N-（苯磺酰基）-N-苯基甘氨酸5，N-（苯磺酰基）-2-苯基甘氨酸6和N-（苯磺酰基）邻氨基苯甲酸7作为N-（苯磺酰基）甘氨酸1醛糖还原酶抑制剂的类似物。 。在大鼠晶状体测定中，5的几种衍生物比相应的甘氨酸1表现出更大的抑制活性，表明N-苯基取代增强了对醛糖还原酶的亲和力。5和1的4-苯甲酰氨基类似物的酶动力学评估表明，这些化合物通过相同的机理产生抑制作用。但是，系列5和系列1的化合物之间的相对抑制效能的显着差异可能表明这些化合物不会以完全相同的方式与抑制剂结合位点相互作用。对系列6的各个对映异构体的评估表明，S异构体比相应的R异构体具有更高的活性。另外，除了萘类似物6n以外，该系列的S立体异构体显示出比甘氨酸1更大的抑制能力。邻氨基苯甲酸酯7通常比甘氨酸1活性低，这表明芳族环直接掺入甘氨酸侧。链可能导致对醛糖还原酶的亲和力降低。
• Amidoaromatic ring sulfonamide hydroxamic acid compounds
  申请人：Monsanto Company

  公开号：US06451791B1

  公开（公告）日：2002-09-17

  An amidoaromatic ring sulfonamide hydroxamic acid compound that inter alia inhibits matrix metalloprotease activity is disclosed, as are a treatment process that comprises administering a contemplated amidoaromatic ring sulfonamide hydroxamic acid compound in a MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.

  本发明揭示了一种阻断基质金属蛋白酶活性的酰胺芳香环磺酰胺羟肟酸化合物，以及一种治疗方法，包括向患有与病理性基质金属蛋白酶活性相关病症的宿主投予考虑的酰胺芳香环磺酰胺羟肟酸化合物，其剂量有效地抑制MMP酶活性。
• Thiol sulfonamide metalloprotease inhibitors
  申请人：Abbas S. Zaheer

  公开号：US20050014840A1

  公开（公告）日：2005-01-20

  This invention is directed to proteinase (protease) inhibitors, and more particularly to thiol sulfonamide inhibitors for matrix metalloproteinase 13(MMP-13), compositions of proteinase inhibitors, intermediates for the syntheses of proteinase inhibitors, processes for the preparation of proteinase inhibitors and processes for treating pathological conditions associated with pathological matrix metalloproteinase activity related to MMP-13.

  本发明涉及蛋白酶（蛋白酶）抑制剂，更具体地涉及用于基质金属蛋白酶13（MMP-13）的巯基磺酰胺抑制剂，蛋白酶抑制剂的组合物，用于合成蛋白酶抑制剂的中间体，制备蛋白酶抑制剂的过程以及用于治疗与MMP-13相关的病理性基质金属蛋白酶活性相关的病理状态的过程。
• Aromatic sulfonyl fluorides as peroxygen activators
  申请人：FMC Corporation

  公开号：US04115059A1

  公开（公告）日：1978-09-19

  A process of removing soil and/or stains from fabrics by immersing the fabrics in a peroxygen bleach bath containing as a peroxygen activator an aromatic sulfonyl fluoride of the formula ArSO.sub.2 F, wherein Ar is an aromatic ring system selected from the class consisting of a phenyl group, a naphthyl group, and a heterocyclic group having 1 to 2 rings, each ring containing 5 to 6 members of which 1 to 2 are heteroatoms selected from the class consisting of nitrogen, oxygen and sulfur, said groups optionally bearing substituents selected from the class consisting of nitro, alkyl of 1 to 16 carbon atoms, alkoxy of 1 to 16 carbon atoms, aliphatic carboxamido of 1 to 16 carbon atoms, aliphatic acyl of 1 to 16 carbon atoms, benzamido, benzoyl, chlorine and bromine. Also described are dry blend compositions containing the bleach bath components.

  一种将织物浸泡在过氧化物漂白液中，其中含有芳香磺酰氟作为过氧化物活化剂，式子为ArSO.sub.2 F，其中Ar是选择自苯基、萘基和含有1至2个环的杂环基的芳香环系统，每个环包含5至6个成员，其中1至2个是选择自氮、氧和硫的杂原子，这些基团可选地带有取代基，所述取代基选择自1至16个碳原子的烷基、1至16个碳原子的烷氧基、1至16个碳原子的脂肪酰胺基、1至16个碳原子的脂肪酰基、苯甲酰胺基、苯甲酰基、氯和溴。还描述了包含漂白液组分的干混合物组合物。
• Discovery of TP0597850: A Selective, Chemically Stable, and Slow Tight-Binding Matrix Metalloproteinase-2 Inhibitor with a Phenylbenzamide–Pentapeptide Hybrid Scaffold
  作者：Tomoki Takeuchi、Yusaku Nomura、Tomoko Tamita、Rie Nishikawa、Hiroyuki Kakinuma、Naoki Kojima、Kosuke Hitaka、Yunoshin Tamura、Masafumi Kamitani、Masashi Mima、Akiko Nozoe、Masato Hayashi

  DOI：10.1021/acs.jmedchem.2c01698

  日期：2023.1.12

  discovery of a novel MMP2-selective inhibitor with high chemical stability and slow tight-binding features. Based on the degradation mechanism of our small-molecule–peptide hybrid 1, the tripeptide linker 5-aminopentanoic acid [Ape(5)]–Glu–Asp} of 1 was replaced by a shorter linker (γ-D-Glu). Phenylbenzamide was suitable for the new generation of MMP2 inhibitors as an S1′ pocket-binding group. The

  基质金属蛋白酶 2 (MMP2) 是一种锌依赖性内肽酶，是癌症和纤维化等多种疾病的有希望的靶点。在此，我们报告了一种新型 MMP2 选择性抑制剂的发现，该抑制剂具有高化学稳定性和缓慢的紧密结合特性。基于我们的小分子-肽杂化物1的降解机制，1的三肽接头 5-氨基戊酸 [Ape(5)]–Glu–Asp}被更短的接头 (γ-D-Glu) 取代。苯基苯甲酰胺适合作为新一代 MMP2 抑制剂的 S1' 口袋结合基团。(4 S )-氨基脯氨酸的引入显着提高了化学稳定性，同时由于其与 Glu130 的相互作用而保持了高亚型选择性。TP0597850 ( 18) 在广泛的 pH 值范围内表现出高稳定性以及有效的 MMP2 抑制 ( K i = 0.034 nM) 和使用抑制常数确定的 ≥ 2000 倍选择性。动力学分析表明它具有缓慢的紧密结合性质和较长的 MMP2 解离半衰期 ( t 1/2 = 265