Benzo[b]thiophene-6-carbonyl chloride | 56540-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: Benzo[b]thiophene-6-carbonyl chloride
• 英文别名: 1-benzothiophene-6-carbonyl chloride
• CAS: 56540-54-6
• 化学式: C₉H₅ClOS
• 分子量: 196.657
• InChiKey: DXLLLMDKDDGBFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzo[b]thiophene-6-carbonyl chloride 在 sodium azide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 Benzo[b]thiophene-6-carbonyl azide
  参考文献：
  名称：

  1,3-Disubstituted Benzazepines as Novel, Potent, Selective Neuropeptide Y Y1 Receptor Antagonists

  摘要：

  A novel series of potent and selective non-peptide neuropeptide Y (NPY) Y1 receptor antagonists, having benzazepine nuclei, have been designed, synthesized, and evaluated for activity. Chemical modification of the R-1 and R-3 substituents in structure 1 (Chart 1) yields several compounds that show high affinity for the Y1 receptor (K-i values of less than 10 nM). SAR studies revealed that introduction of an isopropylurea group at R-1 and a 3-(benzo-condensed-urea) group, 3-(fluorophenylurea) group, or a 3-(N-(4-hydroxyphenyl)guanidine) group at R-3 in structure 1 afforded potent and subtype-selective NPY Y1 receptor antagonists. 3-(3-(Benzothiazol-6-yl)ureido)-1-N-(3-(N'-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (21), which was one of the most potent derivatives, competitively inhibited specific [I-125]peptide YY (PW) binding to Y1 receptors in human neuroblastoma SK-N-MC cells (K-i = 5.1 nM). 21 not only inhibited the Y1 receptor-mediated increase in cytosolic free Ca2+ concentration in SK-N-MC cells but also antagonized the Y1 receptor-mediated inhibitory effect of peptide YY on gastrin-induced histamine release in rat enterochromaffin-like cells. 21 showed no significant affinity in 17 receptor binding assays including Y2, Y4, and Y5 receptors.

  DOI：

  10.1021/jm990044m
• 作为产物：
  描述：

  苯并[b]噻吩-6-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 Benzo[b]thiophene-6-carbonyl chloride
  参考文献：
  名称：

  一类杂环化合物，其制备及用途

  摘要：

  本发明涉及溴结构域抑制剂，提供了一种由通式I表示的化合物、其可药用的盐、对映异构体、非对映异构体、阻转异构体、外消旋体、多晶型物、溶剂合物或经同位素标记之化合物(包括氘取代)，其制备方法，包含其的药物组合物及它们在制药中的用途。

  公开号：

  CN111377934B

文献信息

• Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight
  作者：Haifang Meng、Huiying Xu、Zhi Zhou、Zhenhao Tang、Yidi Li、Yu Zhou、Wei Yi、Xiaowei Wu

  DOI：10.1039/d2gc02347d

  日期：——

  sustainability and applications. Described herein is a robust and convenient rhodium-catalyzed regioselective C–H activation/[4 + 2] annulation for the synthesis of isoquinolones with salient features including a recyclable catalytic reaction system, unique regioselectivity, gram-scale synthesis with low catalyst loading (e.g., 0.5 mol%), ethanol as the green solvent, air and water compatibility, and

  C-H 活化提供了一种直接的方法来构建新的化学键和特权杂环。然而，由于共同的缺陷，C-H活化在可持续性和应用方面仍然面临着巨大的挑战。本文描述了一种稳健且方便的铑催化区域选择性 C-H 活化/[4 + 2] 环化，用于合成异喹诺酮类药物，其显着特征包括可回收的催化反应系统、独特的区域选择性、具有低催化剂负载量的克级合成（例如, 0.5 mol%), 乙醇作为绿色溶剂, 空气和水相容, 纯化过程简单。基于综合实验和 DFT 研究，阐明了羟基和新戊酰部分在两种底物中的作用、炔丙醇伴侣的额外关键功能以及独特化学选择性的起源。此外，还合理地推导出了与羟基和新戊酰基部分连接的独特氢键网络，用于通过随后的 IMH 分析赋予观察到的反向区域选择性。
• Geminal substituted quinuclidine amide compounds as agonists of α-7 nicotonic acetylcholine receptors
  申请人：AXOVANT SCIENCES GMBH

  公开号：US10183938B2

  公开（公告）日：2019-01-22

  The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7-nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

  本发明涉及适用于作为α7-nAChR的激动剂或部分激动剂的新型宝石取代喹吖啶酰胺化合物及其药物组合物，以及制备这些化合物和组合物的方法，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物的方法。特别是，将化合物或组合物施用给有需要的患者的方法，例如，有认知缺陷和/或希望提高认知功能的患者，这些患者可从中获益。
• Cobalt-Catalyzed 2-(1-Methylhydrazinyl)pyridine-Assisted C–H Alkylation/Annulation: Mechanistic Insights and Rapid Access to Cyclopenta[<i>c</i>]isoquinolinone Derivatives
  作者：Hongbin Zhai、Miao Liu、Chao Wang、Shuxian Qiu、Jian Wei、Hongjian Yang、Yundong Wu

  DOI：10.1021/acs.joc.1c01658

  日期：2021.11.5
• Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis
  作者：Belhu B. Metaferia、Satyajit Ray、Jeremy A. Smith、Carole A. Bewley

  DOI：10.1016/j.bmcl.2006.10.031

  日期：2007.1

  The Staudinger reaction between a polymer-supported triphenylphosphine reagent and pseudo-disaccharide azides is successfully applied to synthesize a variety of substrate-mimic mycothiol analogs. Screening of this new group of analogs against the mycobacterial detoxification enzyme mycothiol-S-conjugate amidase (MCA) yielded several modest inhibitors (IC50 values around 50 mu M) and provided additional structure-activity relationships for future optimization of inhibitors of MCA and its homologs. (c) 2006 Published by Elsevier Ltd.
• Novel 3,4-Isoxazolediamides as Potent Inhibitors of Chaperone Heat Shock Protein 90
  作者：Riccardo Baruchello、Daniele Simoni、Giuseppina Grisolia、Giuseppina Barbato、Paolo Marchetti、Riccardo Rondanin、Stefania Mangiola、Giuseppe Giannini、Tiziana Brunetti、Domenico Alloatti、Grazia Gallo、Andrea Ciacci、Loredana Vesci、Massimo Castorina、Ferdinando M. Milazzo、Maria L. Cervoni、Mario B. Guglielmi、Marcella Barbarino、Rosanna Foderà、Claudio Pisano、Walter Cabri

  DOI：10.1021/jm201155e

  日期：2011.12.22

  A structural investigation on the isoxazole scaffold led to the discovery of 3,4-isoxazolediamide compounds endowed with potent Hsp90 inhibitory properties. We have found that compounds possessing a nitrogen atom directly attached to the C-4 heterocycle ring possess in vitro Hsp90 inhibitory properties at least comparable to those of the structurally related 4,S-diarylisoxazole derivatives. A group of compounds from this series of diamides combine potent binding affinity and cell growth inhibitory activity in both series of alkyl- and aryl- or heteroarylarnides, with IC50 in the low nanomolar range. The 3,4-isoxazolediamides were also very effective in causing dramatic depletion of the examined client proteins and, as expected for the Hsp90 inhibitors, always induced a very strong increase in the expression levels of the chaperone Hsp70. In vivo studies against human epidermoid carcinoma A431 showed an antitumor effect of morpholine derivative 73 comparable to that induced by the reference compound 10.