N-(isoquinolin-5-yl)benzamide

• 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)benzamide
• 英文别名: N-[5]isoquinolyl-benzamide；N-[5]Isochinolyl-benzamid；N-isoquinolin-5-ylbenzamide
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: KMWYZNCEVAIHRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(isoquinolin-5-yl)benzamide 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 1.0h， 以96%的产率得到
  参考文献：
  名称：

  新型 2-取代噻唑并 [4,5-f] 异喹啉/喹啉和苯并 [1,2-d:4,3-d'] 双噻唑的合成及其作为 COX-1 和 COX-2 抑制剂的潜力

  摘要：

  2-取代的噻唑并[4,5-f]异喹啉、噻唑并[4,5-f]喹啉和苯并[1,2-d:4,3-d']双噻唑的高效、通用合成已由5硝基异喹啉完成/喹啉和 6-硝基苯并噻唑，所有产品均已通过光谱（IR、H 和 C NMR、LR/HR EI/FAB/ESI-MS）彻底鉴定。噻唑并[4,5-f]异喹啉的合成是此类杂芳烃的首次合成。对涵盖所有三种类型的 18 种化合物进行了 COX-1 和 COX-2 抑制筛选，其中一些表现出中等活性。

  DOI：

  10.3998/ark.5550190.0011.b22
• 作为产物：
  描述：

  5-硝基异喹啉 在 乙醇 、 镍 、 sodium carbonate 作用下， 80.0 ℃ 、12.75 MPa 条件下， 生成 N-(isoquinolin-5-yl)benzamide
  参考文献：
  名称：

  Derivatives of Aminoisoquinolines¹

  摘要：

  DOI：

  10.1021/ja01256a012

文献信息

• Radical C−H Acylation of Nitrogen Heterocycles Induced by an Aerobic Oxidation of Aldehydes
  作者：Subhasis Paul、Manotosh Bhakat、Joyram Guin

  DOI：10.1002/asia.201900857

  日期：2019.9.16

  ketones is described herein. The reaction involves cross-dehydrogenative coupling between aldehydes and heteroaromatic bases with molecular oxygen (O2 ). The key aspect of the method is the generation of reactive acyl radical via homolytic activation of aldehyde C-H bond using O2 as the sole oxidant. The reaction has a good substrate scope with respect to aldehydes and functionalized nitrogen heterocycles

  本文描述了用于合成不对称杂芳基酮的需氧自由基方法。该反应涉及醛和杂芳族碱与分子氧（O2）之间的交叉脱氢偶联。该方法的关键方面是使用O2作为唯一氧化剂，通过醛CH键的均质活化来生成反应性酰基基团。关于醛和官能化的氮杂环，该反应具有良好的底物范围。根据我们的机理研究，建议该反应采用自由基链途径。该方法的合成应用在天然生物碱（±）安格西汀的形式合成中得到了证明。
• [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。
• INHIBITORS OF TRYPTOPHAN-2,3-DIOXYGENASE OR INDOLEAMINE-2,3-DIOXYGENASE
  申请人：IOmet Pharma Ltd.

  公开号：US20180037553A1

  公开（公告）日：2018-02-08

  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 X 1 , X 2 , and X 7 , may be the same or different and each is independently selected from C and N; X 3 , X 4 , X 5 , and X 6 may be the same or different and each is independently selected from C, N, O and S wherein when X 3 is N it has a double bond and wherein when X 6 is N it has a double bond; the dotted line is a bond which may be present or absent; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 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 R 2 , R 3 , R 4 and R 6 comprises a group Y; and provided that the number of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 groups present is such that the respective valencies of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 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 R 31 and R 32 may be the same or different and are selected from H and a substituted or unsubstituted organic group, X 8 is selected from C and N, and each R 313 may be the same or different and is selected from H and a substituted or unsubstituted organic group.
• An expedient synthesis of novel 2-substituted thiazolo[4,5-f]isoquinolines/quinolines and benzo[1,2-d:4,3-d']bisthiazoles and their potential as inhibitors of COX-1 and COX-2
  作者：Manas Chakrabarty、Ajanta Mukherji、Sulakshana Karmakar、Ratna Mukherjee、Kenichiro Nagai、Athina Geronikaki、Pitta Eleni

  DOI：10.3998/ark.5550190.0011.b22

  日期：——

  efficient, general synthesis of 2-substituted thiazolo[4,5-f]isoquinolines, thiazolo[4,5-f]quinolines and benzo[1,2-d:4,3-d′]bisthiazoles has been accomplished from 5nitroisoquinoline/quinoline and 6-nitrobenzothiazole, respectively, and all the products have been thoroughly identified spectroscopically (IR, H and C NMR, LR/ HR EI/ FAB/ ESI-MS). The synthesis of thiazolo[4,5-f]isoquinolines constitutes the

  2-取代的噻唑并[4,5-f]异喹啉、噻唑并[4,5-f]喹啉和苯并[1,2-d:4,3-d']双噻唑的高效、通用合成已由5硝基异喹啉完成/喹啉和 6-硝基苯并噻唑，所有产品均已通过光谱（IR、H 和 C NMR、LR/HR EI/FAB/ESI-MS）彻底鉴定。噻唑并[4,5-f]异喹啉的合成是此类杂芳烃的首次合成。对涵盖所有三种类型的 18 种化合物进行了 COX-1 和 COX-2 抑制筛选，其中一些表现出中等活性。