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: N-(isoquinolin-5-yl)benzenesulfonamide
• 英文别名: N-isoquinolin-5-ylbenzenesulfonamide
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: UTMDVMQLHKONTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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 、 苯硼酸 在 potassium pyrosulfite 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以54%的产率得到N-(isoquinolin-5-yl)benzenesulfonamide
  参考文献：
  名称：

  磺酰胺的连续CS和SN偶联方法。

  摘要：

  描述了涉及硝基芳烃，（杂）芳基硼酸和焦亚硫酸钾的一锅三组分反应，生成磺酰胺。通过不需要金属催化剂的连续CS和SN偶联，获得了具有不同反应性官能团的多种磺酰胺，收率好至极好。

  DOI：

  10.1021/acs.orglett.0c00183

文献信息

• 一种硝基芳烃和硼酸化合物偶联合成磺酰胺 化合物的方法
  申请人：浙江大学

  公开号：CN110372463B

  公开（公告）日：2020-06-30

  本发明属于有机合成领域，具体公开了一种硝基芳烃和硼酸化合物偶联合成磺酰胺化合物的方法，包括：在有机溶剂中，以焦亚硫酸盐为SO2来源，升温进行偶联反应，再经过后处理得到磺酰胺化合物；本发明方法操作简单，无需氮气保护，空气下即可进行，硝基芳烃和硼酸化合物来源丰富，价格相对低廉，反应收率高，底物适用性广，无金属残留。本发明方法可用于合成一系列磺酰胺化合物，合成的化合物在农药、医药等领域均有广泛的应用价值。
• Cu‐Catalyzed Coupling Reactions of Sulfonamides with (Hetero)Aryl Chlorides/Bromides
  作者：Qiaoli Li、Lanting Xu、Dawei Ma

  DOI：10.1002/anie.202210483

  日期：2022.10.24

  of (hetero)aryl halides proceeds with excellent reaction scope by using oxalamides or 4-hydroxypicolinamides as the ligands. For bromides, only 2–5 mol % CuI and oxalamides were required. For chlorides, increasing catalytic loadings to 10 mol % Cu2O and ligands was needed. Direct sulfonamidation of four chloro-containing marketed drugs and preparation of two sulfonamide drugs were achieved under these

  通过使用草酰胺或 4-羟基吡啶甲酰胺作为配体，Cu 催化的（杂）芳基卤化物磺酰胺化反应具有出色的反应范围。对于溴化物，仅需要 2–5 mol% CuI 和草酰胺。对于氯化物，需要将催化负载增加到 10 mol% Cu 2 O 和配体。在此条件下实现了四种含氯市售药物的直接磺酰胺化和两种磺胺类药物的制备。
• 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