N-(tert-butyl)-1H-indole-2-carboxamide | 1155088-87-1

• 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-(tert-butyl)-1H-indole-2-carboxamide
• 英文别名: N-tert-butyl-1H-indole-2-carboxamide
• CAS: 1155088-87-1
• 化学式: C₁₃H₁₆N₂O
• mdl: MFCD12193083
• 分子量: 216.283
• InChiKey: JOUAYMZEYMJYQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 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-(tert-butyl)-1H-indole-2-carboxamide 、 diethyl phenacylmalonate 在 copper diacetate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以15%的产率得到
  参考文献：
  名称：

  Cu（OAc）2促进的α-酰基甲基丙二酸酯与吲哚衍生物的氧化交叉脱氢偶联反应，可制取3功能化的吲哚和多环吲哚。

  摘要：

  开发了Cu（OAc）2促进的α-酰基甲基丙二酸酯与吲哚衍生物的氧化交叉脱氢偶联反应。就吲哚而言，区域选择性偶联产物是通过顺序的脱氢-加成-脱氢过程形成的。当第二个亲核中心位于吲哚的2-位时，进一步连续的亲核环化发生，得到多环吲哚衍生物。事实证明，Cu（OAc）2不仅起氧化剂的作用，而且起催化剂的作用。

  DOI：

  10.1021/acs.joc.0c00624
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N-(tert-butyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  酰胺基烷基吲哚作为有力和选择性的多发性硬化症小鼠模型体内功效的选择性大麻素2型受体激动剂。

  摘要：

  选择性CB 2激动剂代表了一种有吸引力的治疗策略，可用于治疗各种疾病，而无需CB 1受体介导的精神病副作用。我们对黑市设计师药物SDB-001进行了合理的优化，从而确定了有效的和选择性的CB 2激动剂。3-氨基烷基吲哚处的7-甲氧基或7-甲硫基取代产生有效的CB 2拮抗剂（27或28，IC 50 = 16-28 nM）。从吲哚环的3位到2位取代酰胺基烷基大大提高了CB 2上的激动剂选择性，而不是CB 1上受体。特别是，化合物57对CB 2受体表现出有效的激动剂活性（EC 50 = 114–142 nM），而对CB 1受体没有明显的激动剂或拮抗剂活性。此外，在多发性硬化症的实验性自身免疫性脑脊髓炎（EAE）小鼠模型中，有57个显着减轻了临床症状并保护了小鼠中枢神经系统免受免疫损伤。

  DOI：

  10.1021/acs.jmedchem.7b00724

文献信息

• Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors
  申请人：Nakajima Suanne

  公开号：US20070060510A1

  公开（公告）日：2007-03-15

  The present invention relates to compounds of Formula I or II, or a pharmaceutically acceptable salt, ester, or prodrug, thereof: which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明涉及公式I或II的化合物，或其药学上可接受的盐、酯或前药，其抑制丝氨酸蛋白酶活性，特别是丝氨酸蛋白酶NS3-NS4A的活性。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，也可用作抗病毒剂。本发明还涉及包含上述化合物的制药组合物，用于治疗丙型肝炎病毒感染的患者。本发明还涉及通过给予本发明化合物的制药组合物来治疗患有丙型肝炎病毒感染的患者的方法。
• Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D₂ Receptor Through Fragmentation of a Bitopic Ligand
  作者：Shailesh N. Mistry、Jeremy Shonberg、Christopher J. Draper-Joyce、Carmen Klein Herenbrink、Mayako Michino、Lei Shi、Arthur Christopoulos、Ben Capuano、Peter J. Scammells、J. Robert Lane

  DOI：10.1021/acs.jmedchem.5b00585

  日期：2015.9.10

  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.
• Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-<i>endo</i>-<i>dig</i> Iodo-Cyclization PathwayCDRI Communication No. 8094
  作者：Sudhir K. Sharma、Anil K. Mandadapu、Brijesh Kumar、Bijoy Kundu

  DOI：10.1021/jo201228t

  日期：2011.8.19

  An efficient and rapid synthetic strategy for the naturally occurring indoloazepinone scaffold via a three-component reaction of indole-2-carboxamides, 1,3-disubstituted propargyl alcohols, and I-2 is described. The strategy involves a C-H functionalization-alkyne activation-intramolecular hydroamidation-deprotonation domino sequence. The salient feature of this sequence is regioselective electrophilic 7-endo-dig iodo-cyclization during the intramolecular hydroamidation to afford a seven-membered azepinone ring annulated to the indole.
• D3 RECEPTOR AGONIST COMPOUNDS; METHODS OF PREPARATION; INTERMEDIATES THEREOF; AND METHODS OF USE THEREOF
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVIC

  公开号：US20220220102A1

  公开（公告）日：2022-07-14

  Disclosed herein are novel compounds including dopamine D 3 receptor agonists, compositions thereof, methods of use thereof, and processes of synthesizing the same. Further disclosed are D 3 R selective agonist compounds, specifically bitopic ligands comprising chirality.
• US7176208B2
  申请人：——

  公开号：US7176208B2

  公开（公告）日：2007-02-13