3-formyl-1-isopropyl-5-methoxyindole

• 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: 3-formyl-1-isopropyl-5-methoxyindole
• 英文别名: 1-isopropyl-5-methoxy-3-indolecarboxaldehyde；1-isopropyl-5-methoxy-1H-indole-3-carbaldehyde；5-methoxy-1-isopropyl-1H-indole-3-carbaldehyde；5-methoxy-1-propan-2-ylindole-3-carbaldehyde
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD07186532
• 分子量: 217.268
• InChiKey: WNFMGSQKONYSKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-crotonoylpiperidine 、 3-formyl-1-isopropyl-5-methoxyindole 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以45.3%的产率得到(2E,4E)-5-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
  参考文献：
  名称：

  Identification and optimization of piperine analogues as neuroprotective agents for the treatment of Parkinson’s disease via the activation of Nrf2/keap1 pathway

  摘要：

  Parkinson's disease (PD) is a slowly progressive and complex neurodegenerative disorder. Up to date, there are no approved drugs that could slow or reverse the neurodegenerative process of PD. Here, we reported the synthesis of series of piperine analogues and the evaluation of their neuroprotective effects against hydrogen peroxide (H2O2) induced damage in the neuron-like PC12 cells. Among these analogues, 3b exhibited the most potent protection effect and its underlying mechanism was further investigated. Further results indicated that the ROS scavenging and cytoprotection effect of 3b might be related to the Nrf2 activation and upregulation of related phase II antioxidant enzymes, such as HO-1 and NQO1. In in vivo study, oral administration (100 mg/kg) of 3b significantly attenuated PD-associated behavioral deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD and protected tyrosine hydroxylase-immunopositive dopaminergic neurons. Our results provided evidence that 3b might be a promising candidate for Parkinson's disease treatment. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112385
• 作为产物：
  描述：

  5-methoxy-1-isopropyl-1H-indole 在 四甲基乙二胺 、 溶剂红 43 、 potassium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以77%的产率得到3-formyl-1-isopropyl-5-methoxyindole
  参考文献：
  名称：

  使用曙红 Y 作为光氧化还原催化剂的可见光促进吲哚 C-3 甲酰化

  摘要：

  已经使用四甲基乙二胺作为碳源和空气作为氧化剂开发了由曙红 Y 催化的可见光介导的吲哚 C-3 甲酰化。该协议在温和条件下显示出对大量官能团的高耐受性，并提供具有良好产量的 3-甲酰化吲哚。这种方法是传统甲酰化方法的一种极具吸引力的替代方法。

  DOI：

  10.1055/a-1777-2556

文献信息

• Synthesis and Antiproliferative Activity of New N-Acylhydrazone Derivatives Containing Benzothiazole and Indole Based Moiety
  作者：Kai Liu、Yangyang Ding、Congmin Kang

  DOI：10.1007/s11094-020-02215-w

  日期：2020.7

  Through a structure-based molecular hybridization strategy, a series of new N-acylhydrazone derivatives containing the benzothiazole and indole based moiety were designed, synthesized and screened for in vitro antiproliferative activity against Hep G2 cancer cell line. One compound (7a) exhibited excellent antiproliferative activity with IC50 values of 0.78 μM against Hep G2. In addition, C-5 substitutions of the indole ring of target compounds might be crucial for their cytotoxic activities. Additionally, the relative configuration of target compounds was confirmed as the E isomer. Further chemical manipulation of derivative 7a can make it possible to obtain new potential antitumor agents.

  通过基于结构的分子杂交策略，设计、合成了一系列新的N-酰基肼衍生物，这些衍生物含有苯并噻唑和吲哚基部分，并进行了体外抗增殖活性筛选，针对Hep G2癌细胞系进行测试。一种化合物（7a）显示出优异的抗增殖活性，其IC50值为0.78 μM。此外，靶化合物吲哚环的C-5取代可能对其细胞毒性活性至关重要。此外，靶化合物的相对构型被确认为E异构体。对衍生物7a的进一步化学改造可能会获得新的潜在抗肿瘤剂。
• (5-MEMBERED)-(5-MEMBERED) OR (5-MEMBERED)-(6-MEMBERED) FUSED RING CYCLOALKYLAMINE DERIVATIVE
  申请人：MSD K.K.

  公开号：EP2319841A1

  公开（公告）日：2011-05-11

  Disclosed are a compound of a formula (I) and its pharmaceutically-acceptable salt: wherein Q is CH or N; R1a, R1b, R1c and R1d are independently a C1-6 alkyl, a halo-C1-6 alkyl, etc.; R2 is a hydrogen atom, etc.; R3 is independently a hydrogen atom, a C1-6 alkyl, etc., or two R3'S, taken together, form a bridge such as methylene, etc.; R4 and R4b are independently a hydrogen atom, a C1-6 alkyl, etc.; Z is a bicyclic aromatic hetero ring, etc.; Ar is a benzene ring, etc.; m1 and m2 are independently 0, 1 or 2; n is an integer of from 1 to 4. The compound and its salt act as a melanin concentrating hormone receptor antagonist, and are useful as a preventive or remedy for central system disorders, cardiovascular disorders, metabolic disorders, etc.

  本发明公开了一种具有化学式（I）及其药用可接受盐的化合物：其中Q为CH或N；R1a、R1b、R1c和R1d独立地为C1-6烷基、卤代C1-6烷基等；R2为氢原子等；R3独立地为氢原子、C1-6烷基等，或两个R3'结合在一起形成例如亚甲基等的桥；R4和R4b独立地为氢原子、C1-6烷基等；Z为双环芳香杂环、等；Ar为苯环等；m1和m2独立地为0、1或2；n为1至4的整数。该化合物及其盐作为黑色素浓集激素受体拮抗剂，并且可用作中枢系统紊乱、心血管紊乱、代谢紊乱等的预防或治疗。
• 5/5-OR 5/6-MEMBERED CONDENSED RING CYCLOALKYLAMINE DERIVATIVE
  申请人：Kishino Hiroyuki

  公开号：US20110124674A1

  公开（公告）日：2011-05-26

  Disclosed are a compound of a formula (I) and its pharmaceutically-acceptable salt: wherein Q is CH or N; R 1a , R 1b , R 1c and R 1d are independently a C 1-6 alkyl, a halo-C 1-6 alkyl, etc.; R 2 is a hydrogen atom, etc.; R 3 is independently a hydrogen atom, a C 1-6 alkyl, etc., or two R 3 's, taken together, form a bridge such as methylene, etc.; R 4a and R 4b are independently a hydrogen atom, a C 1-6 alkyl, etc.; Z is a bicyclic aromatic hetero ring, etc.; Ar is a benzene ring, etc.; m1 and m2 are independently 0, 1 or 2; n is an integer of from 1 to 4. The compound and its salt act as a melanin concentrating hormone receptor antagonist, and are useful as a preventive or remedy for central system disorders, cardiovascular disorders, metabolic disorders, etc.

  本发明公开了一种化合物及其药学上可接受的盐，其化学式为（I）： 其中，Q是CH或N；R1a，R1b，R1c和R1d独立地表示C1-6烷基，卤代C1-6烷基等；R2是氢原子等；R3独立地表示氢原子，C1-6烷基等，或者两个R3共同形成例如亚甲基等的桥；R4a和R4b独立地表示氢原子，C1-6烷基等；Z是双环芳香杂环，等；Ar是苯环等；m1和m2独立地表示0、1或2；n是1至4的整数。该化合物及其盐作为黑色素浓集激素受体拮抗剂，可用于预防或治疗中枢系统疾病、心血管疾病、代谢性疾病等。
• Reaction of 3/2-formylindoles with TOSMIC: formation of indolyloxazoles and stable indolyl primary enamines
  作者：Manas Chakrabarty、Ramkrishna Basak、Yoshihiro Harigaya、Hiroaki Takayanagi

  DOI：10.1016/j.tet.2004.12.022

  日期：2005.2

  3-Fonnylindole and its 1-substituted and 1,5-disubstituted derivatives react with TOSMIC in presence of potassium carbonate in methanol under reflux to furnish 5-(3'-indolyl)oxazoles, new stable E-2-(3'-indolyl)-2-tosylethenamines and two diastereomers of N-[2-(3'-indolyl)- 1,2-dimethoxy]ethylformamides. In contrast, 2-formylskatole furnishes N-(1-tosyl-2-skatolyl)ethenylformamide. (C) 2004 Elsevier Ltd. All rights reserved.
• [EN] (5-MEMBERED)-(5-MEMBERED) OR (5-MEMBERED)-(6-MEMBERED) FUSED RING CYCLOALKYLAMINE DERIVATIVE<br/>[FR] DÉRIVÉ DE CYCLOALKYLAMINE À NOYAUX FUSIONNÉS À (5 CHAÎNONS)-(5 CHAÎNONS) OU (5 CHAÎNONS)-(6 CHAÎNONS)
  申请人：BANYU PHARMA CO LTD

  公开号：WO2010013595A1

  公开（公告）日：2010-02-04

  【課題】　中枢性疾患、循環器系疾患、代謝性疾患用の医薬品として有用な、メラニン凝集ホルモン受容体の拮抗剤を提供することを目的とする。 【解決手段】　式（Ｉ） 【化１】［式中、Ｑは、ＣＨ又はＮを表し、Ｒ１ａ、Ｒ１ｂ、Ｒ１ｃ及びＲ１ｄは、それぞれ独立して、Ｃ１－６アルキル、ハロＣ１－６アルキル等を表し、Ｒ２は、水素原子等を表し、Ｒ３は、それぞれ独立して、水素原子、Ｃ１－６アルキル等を表すか、２つのＲ３が一緒になって、メチレン等のブリッジを形成し、Ｒ４ａ及びＲ４ｂは、それぞれ独立して、水素原子、Ｃ１－６アルキル等を表し、Ｚは、２環性芳香族複素環等を表し、Ａｒは、ベンゼン環等を表し、ｍ１及びｍ２は、独立して、０、１又は２を表し、ｎは、１～４の整数を表す］で表される化合物又は薬学的に許容されるその塩。