octahydro-indolo<2,3-a>quinolizidine

• 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: octahydro-indolo<2,3-a>quinolizidine
• 英文别名: methyl 1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine-1-propanoate；methyl 3-[(1S,12bS)-1-ethyl-3,4,6,7,12,12b-hexahydro-2H-indolo[2,3-a]quinolizin-1-yl]propanoate
• 化学式: C₂₁H₂₈N₂O₂
• 分子量: 340.466
• InChiKey: XHLOEFPVRHBZOE-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  octahydro-indolo<2,3-a>quinolizidine 在 sodium hydroxide 、 亚硝酸特丁酯 、 potassium tert-butylate 作用下， 以 甲醇 、 水 、 乙二醇 、 甲苯 为溶剂， 反应 6.0h， 生成 长春布宁
  参考文献：
  名称：

  Czibula, Laszlo; Nemes, Andras; Visky, Gyoergy, Liebigs Annalen der Chemie, 1993, # 3, p. 221 - 230

  摘要：

  DOI：
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 palladium on activated charcoal 盐酸 、 potassium tert-butylate 、 氢气 、 三氯氧磷 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 萘烷 、 苯 为溶剂， 反应 129.5h， 生成 octahydro-indolo<2,3-a>quinolizidine
  参考文献：
  名称：

  长春花生物碱及相关化合物的合成—XVII 1：从L-色氨酸手性合成长春花生物碱

  摘要：

  从L-色氨酸开始，以良好的总收率和96％的光学纯度精心制备了3 S，17 S-内酰胺11（用于制备（+）-长春胺及其衍生物的中间体）的两个手性合成。

  DOI：

  10.1016/s0040-4020(01)88615-4

文献信息

• Synthesis of Vinca Alkaloids and Related Compounds, XV1) A New Synthetic Route to (+)-Vincaminic and (+)-Apovincaminic Esters
  作者：Lajos Szabó、György Kalaus、Csaba Szántay

  DOI：10.1002/ardp.19833160709

  日期：——

  Esters of types 7 and 8, possessing excellent vasodilating effects, have been prepared. A method has been found for the resolution of methyl ester 7c. A new method is described for the preparation of the lactam (+)‐10 and its conversion to the oxime (+)‐11, from which (+)‐vincamine (1a) and the (+)‐apovincaminic esters 2a,b were synthesized.

  已经制备了具有优异血管舒张作用的 7 和 8 型酯。已找到一种拆分甲酯 7c 的方法。描述了一种制备内酰胺 (+) - 10 及其转化为肟 (+) - 11 的新方法，从中可以得到 (+) - 长春胺 (1a) 和 (+) - 脱辅酶长春胺酯 2a、b合成的。
• Synthesis of vinca alkaloids and related compounds XXVII formation of a stable 3-acylindolenine
  作者：Zsuzsanna Kardos-Balogh、Ferenc Sóti、Mária Incze、Mária Kajtár、Mária Kajtár-Peredy、Csaba Szántay

  DOI：10.1016/s0040-4039(01)80896-0

  日期：1985.1

  A stable 3-acylindolenine derivative (2) has been prepared intramolecular electrophilic acylation. The reactivity of 2 has been studied.

  稳定的3-acylindolenine衍生物（2）已制备分子内亲电酰化。已经研究了2的反应性。
• Analogs of vincamine and uses thereof
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US11130764B2

  公开（公告）日：2021-09-28

  The present disclosure provides compounds of any one of Formulae (I′), (I), (IA), (II′), (II), (IIA), (IIIA), (III″), (III′), (III), (IIIA), (IV), (V′), (V), (VI), (VII), (VIII′), (VIII), (IX′), (IX), and (X). The compounds described herein may be useful in treating and/or preventing a broad range of diseases (e.g., proliferative disease (e.g., cancers (e.g., non-small cell lung cancer, or glioma), inflammatory diseases, autoimmune diseases), CNS disorder (e.g., drug addiction), metabolic disorder (e.g., diabetes), or infectious disease (e.g., bacterial infection or parasitic infection (e.g., malaria))). Also provided in the present disclosure are pharmaceutical compositions, methods of synthesis of a compound described herein, kits, methods, and uses including or using a compound described herein.

  (III″）、（III′）、（III）、（IIIA）、（IV）、（V′）、（V）、（VI）、（VII）、（VIII′）、（VIII）、（IX′）、（IX）和（X）。本文所述化合物可用于治疗和/或预防多种疾病（如增殖性疾病（如癌症（如非小细胞肺癌或胶质瘤）、炎症性疾病、自身免疫性疾病）、中枢神经系统疾病（如药物成瘾）、代谢性疾病（如糖尿病）或传染性疾病（如细菌感染或寄生虫感染（如疟疾）））。本公开还提供了药物组合物、本文所述化合物的合成方法、试剂盒、方法以及包括或使用本文所述化合物的用途。
• Stereocontrolled Elaboration of Quaternary Carbon Centers through the Asymmetric Michael-Type Alkylation of Chiral Imines/Secondary Enamines:  Enantioselective Synthesis of (+)-Vincamine
  作者：Didier Desmaële、Khalid Mekouar、Jean d'Angelo

  DOI：10.1021/jo9622690

  日期：1997.6.13

  An enantioselective synthesis of (+)-vincamine (1) has been developed. The key strategic element was the stereocontrolled elaboration of a quaternary carbon center (future C-20 center of 1) by using the asymmetric Michael reaction involving chiral imines/secondary enamines under neutral conditions. Thus, addition of enaminolactam (S)-12, derived from ketolactam 7 (itself prepared in four steps from commercially available tryptamine) and (S)-1-phenylethylamine, to methyl acrylate led, after hydrolytic workup, to adduct (R)-6 with a 90% stereoselectivity. The critical removal of the additional keto group of 6 was then examined. After extensive experimentation, we finally established that the most efficient deoxygenation procedure was the Wolff-Kishner reduction of the corresponding keto acid, which proceeded with a 55% yield. The cornerstone [ABD]-tricyclic lactam ester 38 thus obtained was next cyclized under Bischler-Napieralski reaction conditions to afford, after catalytic hydrogenation of the intermediary iminium perchlorate salt, a mixture of the desired, known indoloquinolizidine 5 and its epimer 39, in a ratio of 6:1, respectively. Basic treatment of 5 led to (+)-homoeburnamonine 4, which was finally converted, according to a known procedure, into our goal (+)-vincamine (1). Thus, synthesis of (+)-vincamine (1) has been achieved by a linear sequence of 15 chemical operations, starting from tryptamine, with an overall yield of 1.2%.
• Irie, Kunihiko; Ban, Yoshio, Heterocycles, 1982, vol. 18, p. 255 - 258
  作者：Irie, Kunihiko、Ban, Yoshio

  DOI：——

  日期：——