5-chloro-1-tosyl-1H-indole-3-carbaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-1-tosyl-1H-indole-3-carbaldehyde
• 英文别名: 5-Chloro-1-(4-methylphenyl)sulfonylindole-3-carbaldehyde；5-chloro-1-(4-methylphenyl)sulfonylindole-3-carbaldehyde
• 化学式: C₁₆H₁₂ClNO₃S
• 分子量: 333.795
• InChiKey: BAXXFALNGJKGKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-1-tosyl-1H-indole-3-carbaldehyde 在 二碘甲烷 、 2-(diphenoxyphosphoryl)acetate 、 diethylzinc 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 (1R,2S)-2-(5-chloro-1-tosyl-1H-indol-3-yl)cyclopropane carbaldehyde
  参考文献：
  名称：

  Enantioselective Synthesis of Cyclohepta[b]indoles: Gram-Scale Synthesis of (S)-SIRT1-Inhibitor IV

  摘要：

  An enantioselective gram-scale synthesis of one of the most potent SIRT1-inhibitors has been accomplished by an unprecedented domino reaction sequence establishing the cyclohepta[b]indole core. This method was developed for application in natural product synthesis of a variety of indole alkaloids.

  DOI：

  10.1021/ol4026217
• 作为产物：
  描述：

  5-氯吲哚 在 sodium hydride 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 7.5h， 生成 5-chloro-1-tosyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  新型吲哚衍生物含3-亚甲基二氢呋喃-2（3H）-不可逆LSD1抑制剂的发现与合成

  摘要：

  赖氨酸特异性脱甲基酶1（LSD1），针对单和二甲基化组蛋白3赖氨酸4的脱甲基酶，已成为肿瘤学中有希望的靶标。更具体地说，已证明它是急性髓细胞性白血病（AML）的关键启动子，并且几种LSD1抑制剂已进入治疗AML的临床试验。在本文中，基于通过我们内部化合物库的高通量筛选获得的先导化合物，设计和合成了一系列新的吲哚衍生物。在合成化合物中，9e被表征为具有IC 50的有效LSD1抑制剂浓度为1.230μM，可有效抑制THP-1细胞的增殖。最重要的是，这是第一种不可逆的LSD1抑制剂，它不是单胺氧化酶抑制剂衍生的。因此，发现9e可以作为AML治疗的概念证明工作。

  DOI：

  10.1016/j.ejmech.2019.04.065

文献信息

• [EN] N-ARYLSULFONYL-3-SUBSTITUTED INDOLES HAVING SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM<br/>[FR] INDOLES N-ARYLSULFONYL-3-SUBSTITUES PRESENTANT UNE AFFINITE POUR LE RECEPTEUR DE LA SEROTONINE, METHODE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE CONTENANT CES INDOLES
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004048330A1

  公开（公告）日：2004-06-10

  The present invention relates to novel N-arylsulfonyl-3-substituted indole compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their geometric forms, their N-oxides, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel N-arylsulfonyl-3-substituted indoles of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, and pharmaceutically acceptable compositions containing them. This invention also relates to the process for preparing compounds of the general formula (I), pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine. This invention also relates to the novel intermediates involved therein and process of their preparation.

  本发明涉及新型的N-芳基亚磺酰基-3-取代吲哚化合物、其衍生物、类似物、互变异构体、立体异构体、几何异构体、N-氧化物、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明特别涉及具有通用公式(I)的新型N-芳基亚磺酰基-3-取代吲哚、其衍生物、类似物、互变异构体、立体异构体、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明还涉及制备通用公式(I)化合物的过程、含有此类化合物的药物组合物以及此类化合物和组合物在医学中的用途。本发明还涉及其中涉及的新中间体及其制备过程。
• Organocatalytic enantioselective synthesis of C3 functionalized indole derivatives
  作者：Jasneet Kaur、Nasarul Islam、Akshay Kumar、Vimal K. Bhardwaj、Swapandeep Singh Chimni

  DOI：10.1016/j.tet.2016.10.037

  日期：2016.12

  Michael addition reaction of indolylnitroalkenes with 1,3-dicarbonyl compounds has been developed to obtain enantiomerically enriched 3-(2-nitro-1-(1-tosyl-1H-indol-3-yl)ethyl)pentane-2,4-dione derivatives in up to 98% ee using BnCPN as an organocatalyst. The transition state structure has been predicted using DFT calculation.

  已经开发了吲哚基硝基烯烃与1，3-二羰基化合物的高对映选择性迈克尔加成反应，以获得对映体富集的3-（2-硝基-1-（1-甲苯磺酰基-1 H-吲哚-3-基）乙基）戊烷-2使用BnCPN作为有机催化剂，可在高达98％ee的条件下得到1,4-二酮衍生物。已经使用DFT计算预测了过渡状态结构。
• Catalyst-Free Synthesis of Aminals from Indole-Derived α,α-Di­cyanoolefins
  作者：Hai-Lei Cui、Yin Shi、Hui-Qing Deng、Jin-Ju Lei、Xing-Jie Xu、Xu Tian、Jie Qiao、Lin Zhou

  DOI：10.1055/s-0037-1611940

  日期：2019.1

  We have developed an efficient synthesis of indole fused aminals with nucleophilic imines and indole-derived α,α-dicyanoolefins via N-sulfonyl group transfer. The combination of two privileged frameworks, tetrahydroisoquinoline or tetrahydro-β-carboline and indole, can be realized by this approach to the construction of aminals. The synthetic application of this method was further demonstrated by the

  我们开发了一种通过 N-磺酰基转移有效合成吲哚稠合胺与亲核亚胺和吲哚衍生的 α,α-二氰基烯烃的方法。通过这种构建胺的方法可以实现四氢异喹啉或四氢-β-咔啉和吲哚这两个特权框架的组合。通过腈部分的氧化裂解直接转化为具有羰基的高度官能化的胺醛进一步证明了该方法的合成应用。
• One-pot sequential multicomponent reaction between <i>in situ</i> generated aldimines and succinaldehyde: facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles
  作者：Anoop Singh、Nisar A. Mir、Sachin Choudhary、Deepika Singh、Preetika Sharma、Rajni Kant、Indresh Kumar

  DOI：10.1039/c8ra01637b

  日期：——

  An efficient sequential multi-component method for the synthesis of N-arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and in situ generated Ar/HetAr/indolyl-imines, followed by IBX-mediated oxidative aromatization in one-pot operation. The practical utility of this procedure is shown at gram-scale

  开发了一种有效的连续多组分合成N-芳基吡咯-3-甲醛的方法。该反应涉及琥珀醛和原位生成的 Ar/HetAr/吲哚基亚胺之间脯氨酸催化的直接曼尼希反应环化序列，然后在一锅操作中进行 IBX 介导的氧化芳构化。该方法的实用性以克级显示，并合成了多种生物活性稠合杂环支架，例如吡咯并喹啉、吡咯并恶二唑、二氢吡咯并喹啉和吡咯并菲啶。
• Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with <i>para</i>-Quinone Methides
  作者：Zefeng Song、Weijia Wang、Zhixin Liu、Yue Lu、De Wang

  DOI：10.1021/acs.joc.1c00226

  日期：2021.7.2

  An interesting remote δ-C 1,6-addition and an isomerization cascade reaction for phosphine-catalyzed activated alkynes have been disclosed. The products featuring a functional diene and a 1,1-diaryl methyl motif have been obtained in moderate to good yields (30–86%) by applying para-quinone methides (p-QMs) and δ-substituted alkynoate with tributylphosphine (PnBu3) catalysis, along with high regioselectivity

  已经公开了一种有趣的远程 δ-C 1,6-加成和膦催化的活化炔烃的异构化级联反应。通过应用对醌甲基化物 ( p -QMs) 和 δ-取代的炔酸酯与三丁基膦 (P n Bu 3 ) 催化，以及高区域选择性和立体选择性（dr > 20:1）。广泛的兼容底物（35 个示例），例如吲哚基、羟吲哚基、酯和肉桂基，扩展了该方法的实用性。还介绍了一种合理的机制及其一些应用。