5-甲氧基-1H-吡咯并[3,2-b]吡啶-2-羧醛 | 17288-50-5

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 5-甲氧基-1H-吡咯并[3,2-b]吡啶-2-羧醛
• 中文别名: 5-甲氧基-2-醛基-4-氮杂吲哚
• 英文名称: 2-formyl-5-methoxy-4-azaindole
• 英文别名: 5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde；2-Formyl-5-methoxy-4-aza-indol；5-Methoxy-1H-pyrrolo[3,2-b]pyridine-2-carbaldehyde
• CAS: 17288-50-5
• 化学式: C₉H₈N₂O₂
• mdl: MFCD08448191
• 分子量: 176.175
• InChiKey: CRYWKVXCWDXHPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  363.3±37.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-甲氧基-1H-吡咯并[3,2-b]吡啶-2-羧醛 在 manganese(IV) oxide 、 正丁基锂 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 9.0h， 生成 2-(4-Phenoxybenzoyl)-1,4-dihydropyrrolo[3,2-b]pyridin-5-one
  参考文献：
  名称：

  Structure and activity relationship of 2-(substituted benzoyl)-hydroxyindoles as novel CaMKII inhibitors

  摘要：

  A series of novel 2-substituted-5-hydroxyindoles were synthesized and evaluated for their inhibitory activity against CaMKII. Structure and activity relationship results indicated that potent inhibitory activity could be achieved by modification at the para-position of the phenyl ring of the high throughput screening hit compound 2. Among the prepared compounds, we identified 14 as a novel CaMKII inhibitor with an activity stronger than that of KN-93, a known CaMKII inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.012

文献信息

• (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。
• Synthesis and Chemical Reactivity of 5-Methoxy-2-vinyl-4-azaindoles
  作者：Lourdes Rodriguez-Salvador、Elena Zaballos-Garcia、Eugenia Gonzalez-Rosende、Mohamed Djebouri Sidi、José Sepúlveda-Arques、R. Alan Jones

  DOI：10.1080/00397919708006075

  日期：1997.4

  Abstract 2-Vinyl-4-azaindoles are less reactive with dienophiles than 2-vinylindoles. 5-Methoxy-2-vinyl-4-azaindole 2a and its 1-methyl derivative 2a reacts with N-phenylmaleimide to yield cycloadducts only under vigorous conditions. 2b produces a cycloadduct with dimethyl acetylenedicarboxylate, while 2a yields a Michael-type adduct. Reactions with more reactive dienophiles gave only polymeric products.

  摘要 2-乙烯基-4-氮杂吲哚与亲二烯体的反应性低于2-乙烯基吲哚。5-Methoxy-2-vinyl-4-azaindole 2a 及其 1-甲基衍生物 2a 仅在剧烈条件下与 N-苯基马来酰亚胺反应生成环加合物。2b 与乙炔二羧酸二甲酯生成环加合物，而 2a 生成迈克尔型加合物。与更具反应性的亲双烯体的反应仅产生聚合产物。
• 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。
• INHIBITORS OF APOL1 AND METHODS OF USING SAME
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20220106327A1

  公开（公告）日：2022-04-07

  The disclosure provides at least one entity chosen from compounds of Formula I, a tautomer thereof, a deuterated derivative of that compound or tautomer, and a pharmaceutically acceptable salt of any of the foregoing, compositions comprising the same, and methods of using the same, including uses in treating APOL1-mediated diseases, including pancreatic cancer, focal segmental glomerulosclerosis (FSGS), and/or non-diabetic kidney disease (NDKD).
• [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。