N-isopropyl-1H-indole-5-carboxamide | 953029-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-isopropyl-1H-indole-5-carboxamide
• 英文别名: N-propan-2-yl-1H-indole-5-carboxamide
• CAS: 953029-91-9
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: UQVDVBQSPSAUIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-isopropyl-1H-indole-5-carboxamide 、 (6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)(3-selenocyanatophenyl)methanone 在 copper(l) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 以55.5 %的产率得到3-((3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)selanyl)-N-isopropyl-1H-indole-5-carboxamide
  参考文献：
  名称：

  Design, synthesis, and bioactivity evaluation of novel indole-selenide derivatives as P-glycoprotein inhibitors against multi-drug resistance in MCF-7/ADR cell

  摘要：

  DOI：

  10.1016/j.ejmech.2024.116207
• 作为产物：
  描述：

  吲哚-5-甲酸甲酯 在 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 N-isopropyl-1H-indole-5-carboxamide
  参考文献：
  名称：

  Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand

  摘要：

  Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)-ethyl)cyclohexyl)-1H-indole-2-carboxamide (0269652) (1) adopts a bitopic pose at one protomer of a dopamine D-2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.

  DOI：

  10.1021/acs.jmedchem.5b00585

文献信息

• [EN] BICYCLIC GPR119 MODULATORS<br/>[FR] MODULATEURS DE GPR119 BICYCLIQUES
  申请人：LUPIN LTD

  公开号：WO2012069917A1

  公开（公告）日：2012-05-31

  The present invention relates to compounds of Formula (I) that are useful for treating, preventing and/or managing the diseases, disorders, syndromes or conditions associated with the modulation of GPR119 receptor activity. The invention also relates to the process for preparation of the compounds, pharmaceutical compositions thereof. The invention further relates to methods of treating, preventing and/or managing diseases, disorders syndromes or conditions associated with the modulation of GPR1 19 receptor by using either alone or in combinations of Formula (I).

  本发明涉及一种化合物（I）的公式，该化合物对治疗、预防和/或管理与调节GPR119受体活性相关的疾病、紊乱、综合征或病况有用。该发明还涉及制备这些化合物的方法、其药物组成物。此外，该发明还涉及利用单独或以公式（I）的组合物治疗、预防和/或管理与调节GPR119受体相关的疾病、紊乱、综合征或病况的方法。
• BICYCLIC GPR119 MODULATORS
  申请人：Thotapally Rajesh

  公开号：US20130245000A1

  公开（公告）日：2013-09-19

  The present invention relates to compounds of Formula (I) that are useful for treating, preventing and/or managing the diseases, disorders, syndromes or conditions associated with the modulation of GPR119 receptor activity. The invention also relates to the process for preparation of the compounds, pharmaceutical compositions thereof. The invention further relates to methods of treating, preventing and/or managing diseases, disorders syndromes or conditions associated with the modulation of GPR119 receptor by using either alone or in combinations of Formula (I).

  本发明涉及化合物(I)的使用，该化合物对于治疗、预防和/或管理与GPR119受体活性调节相关的疾病、紊乱、综合症或病况是有用的。本发明还涉及该化合物的制备过程、制药组合物。本发明还涉及使用化合物(I)单独或与其他化合物联合治疗、预防和/或管理与GPR119受体活性调节相关的疾病、紊乱、综合症或病况的方法。
• Bicyclic GPR119 modulators
  申请人：Thotapally Rajesh

  公开号：US09000175B2

  公开（公告）日：2015-04-07

  The present invention relates to compounds of Formula (I) that are useful for treating, preventing and/or managing the diseases, disorders, syndromes or conditions associated with the modulation of GPR119 receptor activity. The invention also relates to the process for preparation of the compounds, pharmaceutical compositions thereof. The invention further relates to methods of treating, preventing and/or managing diseases, disorders syndromes or conditions associated with the modulation of GPR119 receptor by using either alone or in combinations of Formula (I).

  本发明涉及式（I）的化合物，其有助于治疗、预防和/或管理与调节GPR119受体活性相关的疾病、疾病、综合征或疾病。本发明还涉及制备该化合物的过程，以及其制药组合物。本发明还涉及使用式（I）的单独或组合治疗、预防和/或管理与调节GPR119受体相关的疾病、疾病、综合征或疾病的方法。
• Pyrrolidine amide compounds as histone demethylase inhibitors
  申请人：GENENTECH, INC.

  公开号：US10022354B2

  公开（公告）日：2018-07-17

  The present invention relates to compounds useful as inhibitors of one or more histone demethylases, such as KDM5. The invention also provides pharmaceutically acceptable compositions comprising compounds of the present invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及可用作一种或多种组蛋白去甲基化酶（如 KDM5）抑制剂的化合物。本发明还提供了包含本发明化合物的药学上可接受的组合物，以及使用所述组合物治疗各种疾病的方法。
• PYRROLIDINE AMIDE COMPOUNDS AS HISTONE DEMETHYLASE INHIBITORS
  申请人：GENENTECH, INC.

  公开号：US20170312252A1

  公开（公告）日：2017-11-02

  The present invention relates to compounds useful as inhibitors of one or more histone demethylses, such as KDM5. The invention also provides pharmaceutically acceptable compositions comprising compounds of the present invention and methods of using said compositions in the treatment of various disorders.