4-chloro-N-(isoquinolin-5-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-chloro-N-(isoquinolin-5-yl)benzenesulfonamide
• 英文别名: 4-chloro-N-isoquinolin-5-ylbenzenesulfonamide
• 化学式: C₁₅H₁₁ClN₂O₂S
• 分子量: 318.784
• InChiKey: SVIHXNLSVUDCSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-硝基异喹啉 、 4-氯苯硼酸 在 1,10-菲罗啉 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 potassium pyrosulfite 、 异丙醇 作用下， 反应 48.0h， 以61%的产率得到4-chloro-N-(isoquinolin-5-yl)benzenesulfonamide
  参考文献：
  名称：

  铜催化通过插入二氧化硫从硝基芳烃合成磺酰胺。

  摘要：

  硝基芳烃通过插入二氧化硫用作磺酰胺的偶联伙伴。在铜催化下，芳基硼酸，硝基芳烃和偏亚硫酸氢钾的三组分反应平稳进行，从而产生了一系列磺酰胺类化合物，具有良好的收率和优异的收率，具有广泛的底物范围。包括羟基，氰基，氨基和羰基在内的各种官能团都是可以耐受的。提出了一个合理的机理，表明芳基亚磺酸盐是中间体，硝基芳烃和芳基亚磺酸盐的铜辅助相互作用是关键步骤。该方法还扩展到当前市售药物（氟他胺）的后期修饰。

  DOI：

  10.1039/d0cc00721h

文献信息

• [EN] INHIBITORS OF TRYPTOPHAN-2,3-DIOXYGENASE OR INDOLEAMINE-2,3-DIOXYGENASE<br/>[FR] INHIBITEURS DE LA TRYPTOPHANE-2,3-DIOXYGÉNASE OU DE L'INDOLEAMINE-2,3-DIOXYGÉNASE
  申请人：IOMET PHARMA LTD

  公开号：WO2016071283A1

  公开（公告）日：2016-05-12

  Provided is a compound for use in medicine for inhibiting tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO), which compound comprises formula (I) wherein X1, X2, and X7, may be the same or different and each is independently selected from C and N; X3, X4, X5, and X6 may be the same or different and each is independently selected from C, N, O and S wherein when X3 is N it has a double bond and wherein when X6 is N it has a double bond; the dotted line is a bond which may be present or absent; R1, R2, R3, R4, R5, R6, and R7 may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that at least one of R2, R3, R4 and R6 comprises a group Y; and provided that the number of R1, R2, R3, R4, R5, R6, and R7 groups present is such that the respective valencies of X1, X2, X3, X4, X5, X6, and X7 are maintained; and wherein Y is a group having a formula selected from (II), (III), (IV), (V) wherein L may be present or absent, and may be a substituted or unsubstituted organic linking group, and R31 and R32 may be the same or different and are selected from H and a substituted or unsubstituted organic group, X8 is selected from C and N, and each R313 may be the same or different and is selected from H and a substituted or unsubstituted organic group.

  提供的化合物可用于医学中抑制色氨酸-2,3-双加氧酶（TDO）和/或吲哚醇-2,3-双加氧酶（IDO），该化合物包括式（I），其中X1、X2和X7可以相同或不同，每个独立地选择自C和N；X3、X4、X5和X6可以相同或不同，每个独立地选择自C、N、O和S，其中当X3为N时，它具有双键，当X6为N时，它具有双键；虚线是可能存在或不存在的键；R1、R2、R3、R4、R5、R6和R7可以存在或不存在，可以相同或不同，每个独立地选择自H和取代或未取代的有机基团，但至少有一个R2、R3、R4和R6包括一个Y基团；并且提供的R1、R2、R3、R4、R5、R6和R7基团的数量是这样的，以维持X1、X2、X3、X4、X5、X6和X7的相应价；其中Y是具有式（II）、（III）、（IV）、（V）中所选公式的基团，其中L可以存在或不存在，并且可以是取代或未取代的有机连接基团，R31和R32可以相同或不同，选择自H和取代或未取代的有机基团，X8选择自C和N，每个R313可以相同或不同，选择自H和取代或未取代的有机基团。
• Inhibitors of tryptophan-2,3-dioxygenase or indoleamine-2,3-dioxygenase
  申请人：IOmet Pharma Ltd.

  公开号：US10287252B2

  公开（公告）日：2019-05-14

  Provided is a compound for use in medicine for inhibiting tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO), which compound comprises formula (I) wherein X1, X2, and X7, may be the same or different and each is independently selected from C and N; X3, X4, X5, and X6 may be the same or different and each is independently selected from C, N, O and S wherein when X3 is N it has a double bond and wherein when X6 is N it has a double bond; the dotted line is a bond which may be present or absent; R1, R2, R3, R4, R5, R6, and R7 may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that at least one of R2, R3, R4 and R6 comprises a group Y; and provided that the number of R1, R2, R3, R4, R5, R6, and R7 groups present is such that the respective valencies of X1, X2, X3, X4, X5, X6, and X7 are maintained; and wherein Y is a group having a formula selected from (II), (III), (IV), (V) wherein L may be present or absent, and may be a substituted or unsubstituted organic linking group, and R31 and R32 may be the same or different and are selected from H and a substituted or unsubstituted organic group, X8 is selected from C and N, and each R313 may be the same or different and is selected from H and a substituted or unsubstituted organic group.

  本发明提供了一种用于抑制色氨酸-2,3-二氧合酶（TDO）和/或吲哚胺-2,3-二氧合酶（IDO）的药物化合物，该化合物包括式（I） 其中X1、X2和X7可以相同或不同，且各自独立地选自C和N；X3、X4、X5 和 X6 可以相同或不同，各自独立地选自 C、N、O 和 S，其中 X3 为 N 时具有双键，X6 为 N 时具有双键；R1、R2、R3、R4、R5、R6 和 R7 可以存在或不存在，可以相同或不同，且各自独立选自 H 和取代或未取代的有机基团，条件是 R2、R3、R4 和 R6 中至少有一个包含基团 Y；条件是存在的 R1、R2、R3、R4、R5、R6 和 R7 基团的数目使得 X1、X2、X3、X4、X5、X6 和 X7 各自的价维持不变；其中 Y 是具有选自(II)、(III)、(IV)、(V)式的基团 其中 L 可以存在或不存在，并且可以是取代或未取代的有机连接基团，R31 和 R32 可以相同或不同，并且选自 H 和取代或未取代的有机基团，X8 选自 C 和 N，每个 R313 可以相同或不同，并且选自 H 和取代或未取代的有机基团。
• In Vitro and in Vivo Antileishmanial and Trypanocidal Studies of New <i>N</i>-Benzene- and <i>N</i>-Naphthalenesulfonamide Derivatives
  作者：Cristina Galiana-Roselló、Pablo Bilbao-Ramos、M. Auxiliadora Dea-Ayuela、Miriam Rolón、Celeste Vega、Francisco Bolás-Fernández、Enrique García-España、Jorge Alfonso、Cathia Coronel、M. Eugenia González-Rosende

  DOI：10.1021/jm4006127

  日期：2013.11.27

  We report in vivo and in vitro antileishmanial and trypanocidal activities of a new series of N-substituted benzene and naphthalenesulfonamides 1-15. Compounds 1-15 were screened in vitro against Leishmania infantum, Leishmania braziliensis, Leishmania guyanensis, Leishmania amazonensis, and Trypanosoma cruzi. Sulfonamides 6e, 10b, and 10d displayed remarkable activity and selectivity toward T. cruzi epimastigotes and amastigotes. 6e showed significant trypanocidal activity on parasitemia in a murine model of acute Chagas disease. Moreover, 6e, 8c, 9c, 12c, and 14d displayed interesting IC50 values against Leishmania spp promastigotes as well as L. amazonensis and L. infantum amastigotes. 9c showed excellent in vivo activity (up to 97% inhibition of the parasite growth) in a short-term treatment murine model for acute infection by L. infantum. In addition, the effect of compounds 9c and 14d on tubulin as potential target was assessed by confocal microscopy analysis applied to L. infantum promastigotes.
• INHIBITORS OF TRYPTOPHAN-2,3-DIOXYGENASE OR INDOLEAMINE-2,3-DIOXYGENASE
  申请人：Iomet Pharma Ltd.

  公开号：EP3215155B1

  公开（公告）日：2020-10-14
• Copper-catalyzed synthesis of sulfonamides from nitroarenes <i>via</i> the insertion of sulfur dioxide
  作者：Xuefeng Wang、Min Yang、Yunyan Kuang、Jin-Biao Liu、Xiaona Fan、Jie Wu

  DOI：10.1039/d0cc00721h

  日期：——

  Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino

  硝基芳烃通过插入二氧化硫用作磺酰胺的偶联伙伴。在铜催化下，芳基硼酸，硝基芳烃和偏亚硫酸氢钾的三组分反应平稳进行，从而产生了一系列磺酰胺类化合物，具有良好的收率和优异的收率，具有广泛的底物范围。包括羟基，氰基，氨基和羰基在内的各种官能团都是可以耐受的。提出了一个合理的机理，表明芳基亚磺酸盐是中间体，硝基芳烃和芳基亚磺酸盐的铜辅助相互作用是关键步骤。该方法还扩展到当前市售药物（氟他胺）的后期修饰。