4-甲磺酰氨基苯甲酸 | 7151-76-0

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲磺酰氨基苯甲酸
• 中文别名: 4-甲基磺酰胺基苯甲酸
• 英文名称: 4-(methylsulfonamido)benzoic acid
• 英文别名: 4-(methanesulfonamido)benzoic acid；N-(4-carboxyphenyl)methanesulfonamide；4-[(Methylsulfonyl)amino]benzoic acid
• CAS: 7151-76-0
• 化学式: C₈H₉NO₄S
• mdl: MFCD00025052
• 分子量: 215.23
• InChiKey: SROHFTOYGFCJAF-UHFFFAOYSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  408.8±47.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规格使用和储存则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将密封于阴凉干燥处。

制备方法与用途

制备方法

4-甲基磺酰胺基苯甲酸是有机合成的重要中间体，主要用于医药中间体、有机合成和有机溶剂，也可应用于染料生产、农药生产和香料等领域。

用途简介 用途

4-甲基磺酰胺基苯甲酸作为有机合成的重要中间体，广泛用于医药中间体、有机合成和有机溶剂。此外，它还应用于染料生产、农药生产和香料等领域。

反应信息

• 作为反应物：
  描述：

  4-甲磺酰氨基苯甲酸 生成 4-[(methylsulfonyl)amino]benzoic acid sodium salt
  参考文献：
  名称：

  Substituted sulfonamidobenzamides, antiarrhythmic agents and

  摘要：

  本发明涉及一种替代磺酰胺基苯甲酰胺类的小说抗心律失常剂，其通过延长心脏组织的动作电位来治疗心律失常，特别是再入性心律失常。还公开了含有这些化合物的制药配方。

  公开号：

  US04544654A1
• 作为产物：
  描述：

  4-(甲基磺酰胺)苯甲酸甲酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以89%的产率得到4-甲磺酰氨基苯甲酸
  参考文献：
  名称：

  Synthesis and protein kinase C inhibitory activities of balanol analogues with modification of 4-hydroxybenzamido moiety

  摘要：

  A series of racemic balanol analogues with modification of the benzamido moiety of balanol have been synthesized and evaluated for their inhibitory activities against human protein kinase C isozymes (PKC-alpha, -beta I, -beta II, -gamma, -delta, -epsilon, and -eta). The structural modification includes replacement of the 4-hydroxyphenyl group with variously substituted phenyl rings, substitution of the amide linkage with a sulfonamide or an ester, and replacement of the 4-hydroxyphenyl substructure with a hydroxyl substituted indole or a hydroxybenzyl group. In general, these analogues were found to be less potent than balanol, but a number of analogues were identified with improved isozyme selectivity. The structure-activity relationship studies of these analogues also indicated that (1) the optimal general PKC inhibition requires a free 4-hydroxyl group in the benzamido portion of the molecule, (2) the amide linkage of the benzamido moiety is important for PKC inhibition, and (3) the conformation associated with the benzamido moiety seems to have a profound effect on PKC inhibition. The requirement of a free 4-hydroxyl group in conjunction with an appropriate conformation of the benzamido moiety for optimal PKC inhibition suggests that the 4-hydroxyphenyl group may be involved in a specific inhibitor-enzyme interaction important for PKC inhibition. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00125-9

文献信息

• [EN] KCNT1 INHIBITORS AND METHODS OF USE<br/>[FR] INHIBITEURS DE KCNT1 ET PROCÉDÉS D'UTILISATION
  申请人：PRAXIS PREC MEDICINES INC

  公开号：WO2020227097A1

  公开（公告）日：2020-11-12

  The present invention is directed to, in part, compounds and compositions useful for preventing and/or treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene (e.g., KCNT1). Methods of treating a neurological disease or disorder, a disease or condition relating to excessive neuronal excitability, and/or a gain-of-function mutation in a gene such as KCNT1 are also provided herein.

  本发明部分涉及用于预防和/或治疗神经系统疾病或紊乱、与过度神经元兴奋性有关的疾病或症状，以及基因中的功能增强突变（例如，KCNT1）的化合物和组合物。本文还提供了治疗神经系统疾病或紊乱、与过度神经元兴奋性有关的疾病或症状，以及基因中的功能增强突变（如KCNT1）的方法。
• [EN] COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS
  申请人：FOGHORN THERAPEUTICS INC

  公开号：WO2019152437A1

  公开（公告）日：2019-08-08

  The present disclosure features compounds useful for the treatment of BAF complex-related disorders.

  本公开涉及用于治疗BAF复合物相关疾病的化合物。
• 4-(1-hydroxy-2-N-substituted sulfonamido)
  申请人：Allergan, Inc.

  公开号：US05081261A1

  公开（公告）日：1992-01-14

  Compounds of Formula 1, and of Formula 2, ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1.sup.* CO--O--R.sub.1.sup.* CO--NH--R.sub.1.sup.* or PO(OR.sub.1.sup.*).sub.2 or PO(OR.sub.1.sup.*)R.sub.1.sup.* where R.sub.1.sup.* independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; R.sub.2 is H, alkyl of 1 to 20 carbons, or R.sub.2 and Y jointly represent a heterocycle which incorporates the sulfonamide nitrogen in the ring as a heteroatom; R.sub.3 is H or alkyl of 1 to 20 carbons; X is H, R.sub.4, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, CO--N--(R.sub.4).sub.2, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, and R.sub.4 independently is H, phenyl, substituted phenyl, alkyl of 1 to 20 carbons or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy, with a O--COR.sub.4.sup.* group or with a COR.sub.4.sup.* group where R.sub.4.sup.* is H, lower alkyl, OH, OR.sub.4.sup.**, NH.sub.2, NHR.sub.4.sup.** or N(R.sub.4.sup.**).sub.2 group where R.sub.4.sup.** independently is H or lower alkyl, with the proviso that when X is CO--O--R.sub.4 or is CO--NH--R.sub.4 then R.sub.4 is not hydrogen, and Y is H, phenyl or substituted phenyl, or alkyl of 1 to 20 carbons, or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy, O--PO(OR.sub.5).sub.2, O--PO(OR.sub.5)R.sub.5, O--SO.sub.3 H, O--SO.sub.2 R.sub.5, O--COR.sub.5, or COR.sub.5 group where R.sub.5 is H, lower alkyl, OH, OR.sub.5.sup.*, NH.sub.2, NHR.sub.5.sup.* or N(R.sub.5.sup.*).sub.2 group where R.sub.5.sup.* is lower alkyl, or R.sub.2 and Y jointly represent a heterocycle which incorporates the sulfonamide nitrogen in the ring as a heteroatom, with the proviso that when Y is an alkyl substituted with O--PO(OR.sub.5).sub.2 or with O--PO(OR.sub. 5)R.sub.5 then R.sub.5 is not OH, are disclosed. The compounds possess anti-inflammatory activity.

  化合物的化学式1和化学式2如下所示：其中R.sub.1为H或含有1至20个碳原子的烷基，CO--R.sub.1.sup.*，CO--O--R.sub.1.sup.*，CO--NH--R.sub.1.sup.*或PO(OR.sub.1.sup.*).sub.2或PO(OR.sub.1.sup.*)R.sub.1.sup.*，其中R.sub.1.sup.*独立地为H，含有1至20个碳原子的烷基，苯基或取代苯基；R.sub.2为H，含有1至20个碳原子的烷基，或R.sub.2和Y共同代表一个杂环，其中该杂环将磺胺酰胺氮原子作为杂原子；R.sub.3为H或含有1至20个碳原子的烷基；X为H，R.sub.4，CO--R.sub.4，CO--O--R.sub.4，CO--NH--R.sub.4，CO--N--(R.sub.4).sub.2，PO(OR.sub.4).sub.2或PO(OR.sub.4)R.sub.4，其中R.sub.4独立地为H，苯基，取代苯基，含有1至20个碳原子的烷基或含有1至20个碳原子的烷基，其被羟基，烷氧基，取代氨基，硫代烷氧基，O--COR.sub.4.sup.*基或COR.sub.4.sup.*基取代，其中R.sub.4.sup.*为H，低碳烷基，OH，OR.sub.4.sup**，NH.sub.2，NHR.sub.4.sup**或N(R.sub.4.sup**).sub.2基，其中R.sub.4.sup.**独立地为H或低碳烷基，但当X为CO--O--R.sub.4或CO--NH--R.sub.4时，R.sub.4不为氢，Y为H，苯基或取代苯基，含有1至20个碳原子的烷基，或含有1至20个碳原子的烷基，其被羟基，烷氧基，取代氨基，硫代烷氧基，O--PO(OR.sub.5).sub.2，O--PO(OR.sub.5)R.sub.5，O--SO.sub.3 H，O--SO.sub.2 R.sub.5，O--COR.sub.5或COR.sub.5基取代，其中R.sub.5为H，低碳烷基，OH，OR.sub.5.sup*，NH.sub.2，NHR.sub.5.sup*或N(R.sub.5.sup*).sub.2基，其中R.sub.5.sup*为低碳烷基，或R.sub.2和Y共同代表一个杂环，其中该杂环将磺胺酰胺氮原子作为杂原子，但当Y为含有O--PO(OR.sub.5).sub.2或O--PO(OR.sub.5)R.sub.5取代的烷基时，R.sub.5不为OH。这些化合物具有抗炎活性。
• Novel Human Aminopeptidase N Inhibitors: Discovery and Optimization of Subsite Binding Interactions
  作者：Jisook Lee、Natalie B. Vinh、Nyssa Drinkwater、Wei Yang、Komagal Kannan Sivaraman、Luke S. Schembri、Michelle Gazdik、Peter M. Grin、Georgina S. Butler、Christopher M. Overall、Susan A. Charman、Sheena McGowan、Peter J. Scammells

  DOI：10.1021/acs.jmedchem.9b00757

  日期：2019.8.8

  inhibition activities against APN. N-(2-(Hydroxyamino)-2-oxo-1-(3',4',5'-trifluoro-[1,1'-biphenyl]-4-yl)ethyl)-4-(methylsulfonamido)benzamide (6ad) proved to be an extremely potent inhibitor of APN activity in vitro, selective against other zinc-dependent enzymes such as matrix metalloproteases, and possessed limited cytotoxicity against Ad293 cells and favorable physicochemical and metabolic stability properties

  氨基肽酶N（APN / CD13）是锌依赖性的M1氨基肽酶，可通过促进血管生成，转移和肿瘤侵袭来促进癌症进展。我们以前已经确定了含有异羟肟酸的类似物，它们是来自疟疾寄生虫恶性疟原虫M1氨基肽酶（PfA-M1）的APN同源物的有效抑制剂。在这里，我们描述了支持PfA-M1抑制剂作为新型APN抑制剂的再利用的基本原理。使用基于结构的设计方法开发了一系列新型异羟肟酸类似物，并评估了其对APN的抑制活性。N-（2-（羟基氨基）-2-氧代-1-（3'，4'，5'-三氟-[1,1'-联苯] -4-基）乙基）-4-（甲基磺酰胺基）苯甲酰胺（ 6ad）被证明是体外APN活性的极强抑制剂，对其他锌依赖性酶（例如基质金属蛋白酶）具有选择性，对Ad293细胞具有有限的细胞毒性，并具有良好的理化和代谢稳定性能。综合结果表明，化合物6ad可能是抗癌药开发的有用先导。
• Compounds useful as reversible inhibitors of cysteine proteases
  申请人：——

  公开号：US20020058809A1

  公开（公告）日：2002-05-16

  Disclosed are novel cathepsin S, K, F, L and B reversible inhibitory compounds of the formulas (I), (II), (Ia) and (Ib) further defined herein. The compounds are useful for treating autoimmune diseases. Also disclosed are processes for making such novel compounds. 1

  揭示了新型的cathepsin S、K、F、L和B可逆抑制化合物的化学式(I)、(II)、(Ia)和(Ib)，进一步在此处进行了定义。这些化合物可用于治疗自身免疫性疾病。还公开了制备这种新型化合物的方法。

表征谱图