4,9-Dihydro-6-methoxy-pyrano<3,4-b>indol-1(3H)-on | 112585-24-7

• 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: 4,9-Dihydro-6-methoxy-pyrano<3,4-b>indol-1(3H)-on
• 英文别名: 4,9-dihydro-6-methoxy-pyrano[3,4-b]indol-1(3H)-one；6-methoxy-4,9-dihydro-3H-pyrano[3,4-b]indol-1-one
• CAS: 112585-24-7
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: ONCLLVXAPPHDIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,9-Dihydro-6-methoxy-pyrano<3,4-b>indol-1(3H)-on 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0~210.0 ℃ 、4.5 MPa 条件下， 反应 52.0h， 生成 6-methoxy-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Indoles, 6th Mitt. 4,9-Dihydropyrano [3,4-b] indole-1 (3H) -ones 与甲胺的内酰胺化。- 马钱子碱及其衍生物的新合成路线

  摘要：

  可以从 1 和 2 中获得的吡喃并吲哚酮 3a-g 的内酰胺化代表了马钱子碱 (4a) 及其取代衍生物 4b-g、5b、c 的直接合成。还原导致四氢 - β - 咔啉6a – d, f, h。

  DOI：

  10.1002/ardp.19883210708
• 作为产物：
  描述：

  Chloro-(4-methoxyphenyl)diazene 在 盐酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4,9-Dihydro-6-methoxy-pyrano<3,4-b>indol-1(3H)-on
  参考文献：
  名称：

  Synthesis and Evaluations of GLP-1 Secretion and Anti-Diabetic Effect in KKAy Mice of New Tricyclic Compounds

  摘要：

  Glucagon-like peptide-1 (GLP-1), which belongs to the family of incretins, plays important role for the regulation of plasma glucose. Accordingly, GLP-1-based therapies for type 2 diabetes have recognized as one of the most interesting target. In this study, we have found the new tricyclic compounds having strong GLP-1 secretion from human intestinal L cells, and anti-diabetic properties in spontaneously obese and diabetic KKAy mice. The most potent compound 5ka was obtained as the unexpected product, and we would like to report the details of the synthesis, structure elucidations, pharmacological activities on secretion of GLP-1, and anti-diabetic effects using diabetic KKAy mice.

  DOI：

  10.3987/com-14-s(k)29

文献信息

• Indole, 5. Mitt.: 4,9-Dihydro-1-methylimino-3H-pyrano[3,4-b]indole aus 4,9-Dihydropyrano[3,4-b]indol-1(3H)-onen
  作者：Jochen Lehmann、Ursula Pohl

  DOI：10.1002/ardp.19883210307

  日期：——

  Aus den Pyranoindolonen 1a–g und Methylamin erhält man die Hydroxyamide 2a–g. Im Gegensatz zu N‐9‐substituierten Derivaten von 2 können diese nicht über Chloramide zu den Strychnocarpinen 5a–g cyclisiert werden, da mit Thionylchlorid nicht 3a–g sondern die isomeren Imidlacton‐Hydrochloride 4a–g entstehen.

  羟基酰胺 2a-g 是从吡喃并吲哚酮 1a-g 和甲胺中获得的。与 2 的 N-9-取代衍生物相反，它们不能通过氯酰胺环化为马钱子碱 5a-g，因为亚硫酰氯不产生 3a-g，而是生成异构酰亚胺内酯盐酸盐 4a-g。
• Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
  作者：Daisuke Minehira、Daisuke Takeda、Hirokazu Urata、Atsushi Kato、Isao Adachi、Xu Wang、Yuji Matsuya、Kenji Sugimoto、Mayuko Takemura、Satoshi Endo、Toshiyuki Matsunaga、Akira Hara、Jun Koseki、Kayo Narukawa、Shuichi Hirono、Naoki Toyooka

  DOI：10.1016/j.bmc.2011.10.073

  日期：2012.1

  New substituted (1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 mu M) with clinically used epalrestat (IC50 = 0.1 mu M). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 mu M) and very high selectivity for AKR1B1 against AKR1A1 (311: 1) and AKR1B10 (253: 1) compared with epalrestat. (C) 2011 Elsevier Ltd. All rights reserved.
• Lehmann, Jochen; Pohl, Ursula, Archiv der Pharmazie, 1987, vol. 320, # 12, p. 1202 - 1209
  作者：Lehmann, Jochen、Pohl, Ursula

  DOI：——

  日期：——
• Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives
  作者：Michael Decker、Thi Thanh Huyen Nguyen、Jochen Lehmann

  DOI：10.1016/j.tet.2004.03.073

  日期：2004.5

  The mechanism of lactamization of corresponding lactones was investigated by means of gas chromatography and synthesis of possible intermediates as references. Lactones react with amines via the amino acid with subsequent elimination of water to the corresponding lactams. In the first step, also hydroxyamides are in equilibrium with the lactones and amines, respectively, which are not able to form the amide though. This mechanism opens a new approach for the synthesis of N-beta-disubstituted tryptamines. (C) 2004 Elsevier Ltd. All rights reserved.
• LEHMANN, JOCHEN;POHL, URSULA, ARCH. PHARM., 320,(1987) N 12, 1202-1209
  作者：LEHMANN, JOCHEN、POHL, URSULA

  DOI：——

  日期：——