7-甲氧基-1H-吲哚-2-甲醛 | 30464-91-6

• 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: 7-甲氧基-1H-吲哚-2-甲醛
• 英文名称: 7-methoxy-1H-indole-2-carbaldehyde
• 英文别名: 7-methoxy-indole-2-carbaldehyde
• CAS: 30464-91-6
• 化学式: C₁₀H₉NO₂
• mdl: MFCD06800926
• 分子量: 175.187
• InChiKey: GNXQSRRPZKDXHA-UHFFFAOYSA-N

物化性质

• 沸点：
  375.2±22.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-甲氧基-1H-吲哚-2-甲醛 在 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 四丁基溴化铵 、 氢气 、 六甲基二硅氮烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 (E)-N-benzyl-2-(4-hydroxypentyl)-7-methoxy-3-(2-nitroethenyl)indole
  参考文献：
  名称：

  咔唑衍生物的合成-III。分子内迈克尔加成反应合成新的吡咯烷基[3,4-c]咔唑

  摘要：

  我们已经报告了间和分子内合成咔唑的迈克尔加成。1玫瑰树碱衍生物与这些化合物有关，尤其是具有9-甲氧基和9-羟基取代基的玫瑰树碱衍生物表现出明显的抗肿瘤和抗白血病活性。2因此，我们分别从N-苄基-2-甲酰基-5-甲氧基吲哚（2a）和N-苄基-2-甲酰基-7-甲氧基吲哚（2b）开始制备了四氢咔唑7a和7b。

  DOI：

  10.1016/0040-4020(96)00271-2
• 作为产物：
  描述：

  7-甲氧基-1H-吲哚-2-羧酸甲酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.75h， 生成 7-甲氧基-1H-吲哚-2-甲醛
  参考文献：
  名称：

  2-[N-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists

  摘要：

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.

  DOI：

  10.1021/jm970721h

文献信息

• [EN] IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS<br/>[FR] COMPOSÉS IMIDAZO-PYRIDINE À UTILISER EN TANT QU'INHIBITEURS DE PAD
  申请人：JUBILANT BIOSYS LTD

  公开号：WO2019077631A1

  公开（公告）日：2019-04-25

  Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.

  公式（I）、（II）和（III）的杂环化合物以及它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物在本文中被描述。本文描述的化合物、它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物是PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、皮肤红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、多发性硬化和牛皮癣。还描述了制备公式（I）、（II）和（III）的化合物、它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物的过程，以及包含公式（I）、公式（II）、公式（III）的化合物或其药学上可接受的盐的药物组合物。
• Dynamic kinetic resolution of γ,γ-disubstituted indole 2-carboxaldehydes <i>via</i> NHC-Lewis acid cooperative catalysis for the synthesis of tetracyclic ε-lactones
  作者：Kuruva Balanna、Soumen Barik、Sayan Shee、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1039/d2sc03745a

  日期：——

  development of efficient and enantioselective routes to these target compounds. Described herein is the enantioselective synthesis of indole-fused ε-lactones by the N-heterocyclic carbene (NHC)-Lewis acid cooperative catalyzed dynamic kinetic resolution (DKR) of in situ generated γ,γ-disubstituted indole 2-carboxaldehydes. The Bi(OTf)3-catalyzed Friedel–Crafts reaction of indole-2-carboxaldehyde with 2-hydroxy

  ε-内酯在各种生物活性化合物中普遍存在，激发了开发这些目标化合物的有效和对映选择性途径。本文描述的是通过原位生成的γ，γ-二取代吲哚2-甲醛的N-杂环卡宾(NHC)-路易斯酸协同催化动态动力学拆分(DKR)对吲哚稠合ε-内酯的对映选择性合成。 Bi(OTf) 3催化的吲哚-2-甲醛与2-羟基苯基对醌甲基化物的傅克反应生成γ,γ-二取代吲哚2-甲醛，在NHC和Bi(OTf) 3存在下生成γ,γ-二取代吲哚2-甲醛。以高达 93% 的产率和 >99 : 1 er 提供所需的四环 ε-内酯。此外，还对这种形式的[4+3]成环机制进行了初步研究。
• IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS
  申请人：Jubilant Epipad LLC

  公开号：EP3697785A1

  公开（公告）日：2020-08-26
• 2-[<i>N</i>-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists
  作者：Gilberto Spadoni、Cesarino Balsamini、Annalida Bedini、Giuseppe Diamantini、Barbara Di Giacomo、Andrea Tontini、Giorgio Tarzia、Marco Mor、Pier Vincenzo Plazzi、Silvia Rivara、Romolo Nonno、Marilou Pannacci、Valeria Lucini、Franco Fraschini、Bojidar Michaylov Stankov

  DOI：10.1021/jm970721h

  日期：1998.9.1

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.
• Synthesis of carbazole derivatives — III. Synthesis of new pyrrolidino[3,4-c]carbazoles by intramolecular Michael addition
  作者：Sioavosh Mahboobi、Sabine Kuhr、Markus Koller

  DOI：10.1016/0040-4020(96)00271-2

  日期：1996.4

  We have reported on the synthesis of carbazoles by inter- and intramolecular Michael addition.1 Ellipticine derivatives are related to these compounds, and especially those with 9-methoxy- and 9-hydroxy substituents exhibit appreciable antitumor and antileukemic activity.2 Therefore, we have prepared the tetrahydrocarbazoles 7a and 7b, starting from N-benzyl-2-formyl-5-methoxyindole (2a) and N-ben

  我们已经报告了间和分子内合成咔唑的迈克尔加成。1玫瑰树碱衍生物与这些化合物有关，尤其是具有9-甲氧基和9-羟基取代基的玫瑰树碱衍生物表现出明显的抗肿瘤和抗白血病活性。2因此，我们分别从N-苄基-2-甲酰基-5-甲氧基吲哚（2a）和N-苄基-2-甲酰基-7-甲氧基吲哚（2b）开始制备了四氢咔唑7a和7b。