2-chloro-5-methyl-1H-indole-3-carboxaldehyde | 535924-79-9

• 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: 2-chloro-5-methyl-1H-indole-3-carboxaldehyde
• 英文别名: 2-chloro-5-methyl-1H-indol-3-carboxaldehyde；2-chloro-5-methyl-1H-indole-3-carbaldehyde
• CAS: 535924-79-9
• 化学式: C₁₀H₈ClNO
• mdl: MFCD05178169
• 分子量: 193.633
• InChiKey: QOEJIVLRLHTXSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-5-methyl-1H-indole-3-carboxaldehyde 在 4-二甲氨基吡啶 、 sodium hydrogensulfide 、 (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 51.0h， 生成 tert-butyl(6aR,11aR,12S)-12-hydroxy-2-methyl-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide
  参考文献：
  名称：

  有机催化对映选择性串联磺胺-迈克尔/羟醛反应，以访问带有两个连续立体中心的二氢硫吡喃稠合的苯并环丁砜骨架。

  摘要：

  开发了第一个2-巯基吲哚-3-甲醛和2-巯基苯甲醛与苯并[ b ]噻吩砜的有机催化非对映和对映选择性磺胺-迈克尔/羟醛反应。用多种氢键合的硫脲作为催化剂，在温和的反应条件下，可以顺利获得各种多环二氢硫吡喃稠合的苯并砜类化合物，并具有优异的结果（产率高达99％，> 20：1 dr和99％ee）。

  DOI：

  10.1039/d0cc04840b
• 作为产物：
  描述：

  5-甲氧基吲哚 在 三氯氧磷 作用下， 以54 %的产率得到2-chloro-5-methyl-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  ANTI-INFLAMMATORY COMPOSITION COMPRISING BENZOFURAN-BASED N-ACYLHYDRAZONE DERIVATIVES

  摘要：

  The present disclosure relates to a pharmaceutical composition for preventing or treating an inflammatory disease, comprising a benzofuran-based N-acylhydrazone compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. The benzofuran-based N-acylhydrazone compound according to the present disclosure inhibits the activity of NF-κB, which is a major signal transmitter in the inflammatory response, thereby disrupting the initial pathway and process of the biological inflammatory response system and inhibiting inflammatory immune cells and inflammatory cytokines, and thus can prevent and treat various pathological diseases caused by the inflammatory response.

  公开号：

  US20230293487A1

文献信息

• 벤조퓨란계 N-아실히드라존 유도체 및 이를 포함하는 약학적 조성물
  申请人：Korea Research Institute of Bioscience and Biotechnology 한국생명공학연구원(319990341665) BRN ▼314-82-06063

  公开号：KR20210008819A

  公开（公告）日：2021-01-25

  본 발명에 따른 벤조퓨란계 N-아실히드라존 유도체는 우수한 항암 효과를 가지면서 독성이 낮고 용해도가 우수하므로, 이를 포함하는 약학적 조성물은 다양한 암을 비롯한 세포증식성 질환의 예방 또는 치료에 유용하게 사용될 수 있다.

  根据本发明，本发明的苯唑吡喃类N-酰基肼衍生物具有优越的抗癌效果，毒副作用低，溶解度好，因此，包含该物质的药物组合物可以有效地用于预防或治疗包括多种癌症在内的细胞增殖性疾病。
• N-Heterocyclic Carbene-Catalyzed Domino Ring-Opening/Redox Amidation/Cyclization Reactions of Formylcyclopropane 1,1-Diesters: Direct Construction of a 6−5−6 Tricyclic Hydropyrido[1,2-<i>a</i>]indole Skeleton
  作者：Ding Du、Linxia Li、Zhongwen Wang

  DOI：10.1021/jo900650h

  日期：2009.6.5

  Catalyzed by N-heterocyclic carbenes (NHCs), domino ring-opening/redox amidation/cyclization reactions of the readily available formylcyclopropane 1,1-diesters with 2-chloro-1H-indole-3-carboaldehydes were reported. This methodology provides an efficient and direct construction of a 6−5−6 tricyclic hydropyrido[1,2-a]indole skeleton, which can be potentially applied for the synthesis of several types

  据报道，在N-杂环卡宾（NHC）的催化下，易得的甲酰基环丙烷1,1-二酯与2-氯-1 H-吲哚-3-碳醛的多米诺开环/氧化还原酰胺化/环化反应得到了报道。该方法学提供了一种有效的直接构建6-5-6三环氢吡啶并[1,2- a ]吲哚骨架的方法，可潜在地用于合成几种类型的多环吲哚生物碱。
• BENZOFURAN-BASED N-ACYLHYDRAZONE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：Korea Research Institute of Bioscience and Biotechnology

  公开号：EP4015516A1

  公开（公告）日：2022-06-22

  A benzofuran-based N-acylhydrazone derivative according to the present invention has an excellent anticancer effect while having low toxicity and excellent solubility, and thus a pharmaceutical composition comprising the derivative can be usefully used to prevent or treat a cell proliferative disorder including various cancers.

  根据本发明的苯并呋喃基 N-酰腙衍生物具有极佳的抗癌效果，同时毒性低、溶解性好，因此包含该衍生物的药物组合物可以有效地用于预防或治疗包括各种癌症在内的细胞增殖性疾病。
• Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters
  作者：Lei Yang、Jian-Qiang Zhao、Yong You、Zhen-Hua Wang、Wei-Cheng Yuan

  DOI：10.1039/d0cc04840b

  日期：——

  The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, >20 : 1 dr

  开发了第一个2-巯基吲哚-3-甲醛和2-巯基苯甲醛与苯并[ b ]噻吩砜的有机催化非对映和对映选择性磺胺-迈克尔/羟醛反应。用多种氢键合的硫脲作为催化剂，在温和的反应条件下，可以顺利获得各种多环二氢硫吡喃稠合的苯并砜类化合物，并具有优异的结果（产率高达99％，> 20：1 dr和99％ee）。
• ANTI-INFLAMMATORY COMPOSITION COMPRISING BENZOFURAN-BASED N-ACYLHYDRAZONE DERIVATIVES
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US20230293487A1

  公开（公告）日：2023-09-21

  The present disclosure relates to a pharmaceutical composition for preventing or treating an inflammatory disease, comprising a benzofuran-based N-acylhydrazone compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof. The benzofuran-based N-acylhydrazone compound according to the present disclosure inhibits the activity of NF-κB, which is a major signal transmitter in the inflammatory response, thereby disrupting the initial pathway and process of the biological inflammatory response system and inhibiting inflammatory immune cells and inflammatory cytokines, and thus can prevent and treat various pathological diseases caused by the inflammatory response.