methyl (1S,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate | 274677-77-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl (1S,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 274677-77-9
• 化学式: C₃₉H₃₅N₃O₅
• 分子量: 625.724
• InChiKey: MDCZVYAYROAOJR-IUKTVIPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  47
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 吗啉 作用下， 以 四氢呋喃 、 水 、 二氯甲烷 为溶剂， 反应 1.25h， 以67.29%的产率得到(3S,8aS)-3-((2-benzoyl-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  NBS合成吲哚基二酮哌嗪

  摘要：

  由N-溴代琥珀酰亚胺（NBS）作为重要试剂，从1-取代的1,2,3,4-四氢-β-咔啉-3-羧酸甲酯盐酸盐开始合成了两个系列的吲哚基二酮哌嗪。所有八种化合物均通过核磁共振（NMR）和元素分析进行​​了表征。此外，还讨论了NBS反应重排的机制。手性26：790–792，2014。©2014 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22346
• 作为产物：
  描述：

  L-色氨酸甲酯 在 sodium carbonate 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 生成 methyl (1S,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues

  摘要：

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.

  DOI：

  10.1021/jm9905662

文献信息

• Enantioselective Synthesis and Antimicrobial Activities of Tetrahydro-<i>Β</i> -Carboline Diketopiperazines
  作者：Yangmin Ma、Hao Wu、Jin Zhang、Yanchao Li

  DOI：10.1002/chir.22193

  日期：2013.10

  A series of single isomers tetrahydro‐β‐carboline diketopiperazines were stereoselectively synthesized starting from l‐tryptophan methyl ester hydrochloride and six aldehydes through a four‐step reaction including Pictet‐Spengler reaction, crystallization‐induced asymmetric transformations (CIAT), Schotten‐Baumann reaction, and intramolecular ester amidation. The chemical structures were characterized

  从l-色氨酸甲酯盐酸盐和六个醛开始，通过Pictet-Spengler反应，结晶诱导不对称转化（CIAT），Schotten-Baumann反应等四步反应，立体选择性地合成了一系列单一异构体四氢β-咔啉二酮哌嗪和分子内酯酰胺化。化学结构通过核磁共振（NMR）和元素分析进行​​表征，其中两种化合物通过X射线单晶衍射法确定。此外，还测试了所有化合物的抗菌活性。手性25：656–662，2013。©2013 Wiley Periodicals，Inc.
• Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues
  作者：Haishan Wang、Takeo Usui、Hiroyuki Osada、A. Ganesan

  DOI：10.1021/jm9905662

  日期：2000.4.1

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.
• Synthesis of Indolyldiketopiperazines with NBS
  作者：Yangmin Ma、Decheng Ren、Hao Wu、Jin Zhang、Tingting Feng、Yanchao Li

  DOI：10.1002/chir.22346

  日期：2014.12

  Two series of indolyldiketopiperazines were synthesized starting from methyl 1‐substituted‐1,2,3,4‐tetrahydro‐β‐carboline‐3‐carboxylate hydrochlorides via N‐bromo‐succinimide (NBS) as an important reagent. All eight compounds were characterized by nuclear magnetic resonance (NMR) and elemental analysis. Furthermore, the mechanisms of NBS‐reacted rearrangements are also discussed. Chirality 26:790–792

  由N-溴代琥珀酰亚胺（NBS）作为重要试剂，从1-取代的1,2,3,4-四氢-β-咔啉-3-羧酸甲酯盐酸盐开始合成了两个系列的吲哚基二酮哌嗪。所有八种化合物均通过核磁共振（NMR）和元素分析进行​​了表征。此外，还讨论了NBS反应重排的机制。手性26：790–792，2014。©2014 Wiley Periodicals，Inc.