1H-吲哚-5-羰酰氯 | 161397-68-8

• 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
• 中文名称: 1H-吲哚-5-羰酰氯
• 中文别名: 5-羰基氯-1H-吲哚
• 英文名称: 1H-Indole-5-carbonyl chloride
• CAS: 161397-68-8
• 化学式: C₉H₆ClNO
• mdl: MFCD11520769
• 分子量: 179.606
• InChiKey: DJQIAZZRZXXUEB-UHFFFAOYSA-N

物化性质

• 沸点：
  340.3±15.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1H-吲哚-5-羰酰氯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-((1H-indol-5-yl)methyl)morpholine
  参考文献：
  名称：

  Substituted Pentacyclic Carbazolones as Novel Muscarinic Allosteric Agents:  Synthesis and Structure−Affinity and Cooperativity Relationships

  摘要：

  Two series of pentacyclic carbazolones, 22 and 23, have been synthesized utilizing a facile intramolecular Diels-Alder reaction and are allosteric modulators at muscarinic acetylcholine receptors. Their affinities and cooperativities with acetylcholine and the antagonist N-methylscopolamine (NMS) at M-1-M-4 receptors have been analyzed and compared. All of the synthesized compounds are negatively cooperative with acetylcholine. In contrast, the majority of the compounds exhibit positive cooperativity with NMS, particularly at M-2 and M-4 receptors. The subtype selectivity, in terms of affinity, was in general M-2 > M-1 > M-4 > M-3. The largest increases in affinity produced by a single substitution of the core structure were given by the 1-OMe (22b) and 1-Cl (22d) derivatives. The position of the N in the ring did not appear to be important for binding affinity or cooperativity. Two compounds 22y and 23i, both trisubstituted analogues, were the most potent compounds synthesized, with dissociation constants of 30-100 nM for the M-2 NMS-liganded and unliganded receptor, respectively. The results indicate that the allosteric site, like the primary binding site, is capable of high-affinity interactions with molecules of relatively low molecular weight.

  DOI：

  10.1021/jm010946z
• 作为产物：
  描述：

  吲哚-5-羧酸 在 吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 1H-吲哚-5-羰酰氯
  参考文献：
  名称：

  小分子硫酯作为 SARS-CoV-2 主要蛋白酶抑制剂：酶抑制、构效关系、抗病毒活性和 X 射线结构测定

  摘要：

  SARS-CoV-2 的主要蛋白酶（M pro、 3CL pro）是冠状病毒中一个有吸引力的靶点，因为它在病毒复制和转录中发挥着至关重要的作用。在这里，我们报告了作为 SARS-CoV-2 M前抑制剂的新型小分子硫酯的设计、合成和构效关系。化合物3w和3x表现出优异的 SARS-CoV-2 M pro抑制作用，k inac / K i分别为 58,700 M –1 s –1 ( K i = 0.0141 μM) 和 27,200 M –1 s –1 ( K i = 0.0332 μM) ， 分别。在 Calu-3 和 Vero76 细胞中，化合物3h、3i 、 3l、3r、3v、3w和3x显示纳摩尔范围内的抗病毒活性，且没有宿主细胞毒性。完成了3w和3af与 SARS-CoV-2 M pro的共结晶，X 射线结构显示与蛋白酶的催化 Cys145 残基共价结合。有效的 SARS-CoV-2 Mpro

  DOI：

  10.1021/acs.jmedchem.2c00636

文献信息

• A convenient and mild method for 1,2,4-oxadiazole preparation: cyclodehydration of O -acylamidoximes in the superbase system MOH/DMSO
  作者：Sergey Baykov、Tatyana Sharonova、Angelina Osipyan、Sergey Rozhkov、Anton Shetnev、Alexey Smirnov

  DOI：10.1016/j.tetlet.2016.05.071

  日期：2016.6

  Herein, we reported a general, convenient, and efficient synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within short reaction times (10–20 min). In addition, mild reaction conditions and a simple work-up procedure allow the synthesis of a wide range of heat-labile

  在本文中，我们报道了在超碱系统MOH / DMSO（M = Li，Na，K）中通过O-酰基酰胺基肟的环脱水作用，一种一般，便捷，有效的合成3,5-二取代-1,2,4-恶二唑的方法。在较短的反应时间内（10-20分钟）即可获得出色的分离产率（高达98％）。此外，温和的反应条件和简单的后处理程序可以合成多种热不稳定的含1,2,4-恶二唑的物质。
• Opioid and opioid-like compounds and uses thereof
  申请人：Wu S.C. Edwin

  公开号：US20050261329A1

  公开（公告）日：2005-11-24

  The present invention relates to opioid and opioid-like compounds, and pharmaceutical formulations thereof, and use thereof for prevention and treatment of disorders such as septic shock and organ damage.

  本发明涉及阿片类和类阿片化合物，以及它们的药物配方，以及将其用于预防和治疗败血症休克和器官损伤等疾病。
• Heterocyclic N-acetonylbenzamides and their use as fungicides
  申请人：Dow AgroSciences LLC

  公开号：EP1229037A1

  公开（公告）日：2002-08-07

  Certain N-acetonylbenzamides and their use as fungicides are disclosed. The N-acetonylbenzamides disclosed contain a heterocyclic ring fused to an aromatic ring. These compounds are particularly effective against phytopathogenic fungi of the class Oomycetes. Also disclosed is a method for controlling phytopathogenic fungi by applying one or more of the heterocyclic N-acetonylbenzamides of the present invention, optionally with one or more additional fungicidal compounds.

  公开了某些N-乙酰基苯甲酰胺及其作为杀菌剂的用途。所公开的N-乙酰基苯甲酰胺含有与芳香环融合的杂环。这些化合物对卵菌门植物病原真菌特别有效。还公开了一种通过施用本发明的一个或多个杂环N-乙酰基苯甲酰胺以及一个或多个额外杀菌化合物来控制植物病原真菌的方法。
• Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
  作者：Arun K. Ghosh、Gangli Gong、Valerie Grum-Tokars、Debbie C. Mulhearn、Susan C. Baker、Melissa Coughlin、Bellur S. Prabhakar、Katrina Sleeman、Michael E. Johnson、Andrew D. Mesecar

  DOI：10.1016/j.bmcl.2008.08.082

  日期：2008.10

  Design, synthesis and biological evaluation of a series of 5-chloropyridine ester-derived severe acute respiratory syndrome-coronavirus chymotrypsin-like protease inhibitors is described. Position of the carboxylate functionality is critical to potency. Inhibitor 10 with a 5-chloropyridinyl ester at position 4 of the indole ring is the most potent inhibitor with a SARS-CoV 3CLpro IC(50) value of 30

  描述了一系列5-氯吡啶酯衍生的严重急性呼吸综合征-冠状病毒糜蛋白酶样蛋白酶抑制剂的设计、合成和生物学评价。羧酸酯官能团的位置对于效力至关重要。吲哚环 4 位具有 5-氯吡啶酯的抑制剂 10 是最有效的抑制剂，其 SARS-CoV 3CLpro IC(50) 值为 30 nM，抗病毒 EC(50) 值为 6.9 microM。分子对接研究提供了这些抑制剂可能的结合模式。
• Structure–Activity Relationship for the Oxadiazole Class of Antibacterials
  作者：Marc A. Boudreau、Derong Ding、Jayda E. Meisel、Jeshina Janardhanan、Edward Spink、Zhihong Peng、Yuanyuan Qian、Takao Yamaguchi、Sebastian A. Testero、Peter I. O’Daniel、Erika Leemans、Elena Lastochkin、Wei Song、Valerie A. Schroeder、William R. Wolter、Mark A. Suckow、Shahriar Mobashery、Mayland Chang

  DOI：10.1021/acsmedchemlett.9b00379

  日期：2020.3.12

  A structure–activity relationship (SAR) for the oxadiazole class of antibacterials was evaluated by syntheses of 72 analogs and determination of the minimal-inhibitory concentrations (MICs) against the ESKAPE panel of bacteria. Selected compounds were further evaluated for in vitro toxicity, plasma protein binding, pharmacokinetics (PK), and a mouse model of methicillin-resistant Staphylococcus aureus

  通过合成72种类似物并确定对ESKAPE细菌的最小抑菌浓度（MIC）来评估恶二唑类抗菌剂的结构活性关系（SAR）。进一步评估了所选化合物的体外毒性，血浆蛋白结合，药代动力学（PK）和耐甲氧西林金黄色葡萄球菌（MRSA）感染的小鼠模型。恶二唑72c显示出有效的体外抗菌活性，显示出低清除率，高分布量和41％的口服生物利用度，并在MRSA感染的小鼠模型中显示出功效。