(1S,2R,4S,5R)-2-((S)-allyloxy(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane bromide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (1S,2R,4S,5R)-2-((S)-allyloxy(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane bromide
• 英文别名: O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide；O-allyl-N-(9-anthracenylmethyl)cinchoninium bromide；(+)-O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide；4-[(S)-[(2R,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-prop-2-enoxymethyl]quinoline;bromide
• 化学式: Br*C₃₇H₃₇N₂O
• 分子量: 605.618
• InChiKey: QOWNPAUSLGATNL-VYTZWAMGSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 (1S,2R,4S,5R)-1-(anthracen-9-ylmethyl)-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride 在 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以87%的产率得到(1S,2R,4S,5R)-2-((S)-allyloxy(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane bromide
  参考文献：
  名称：

  Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

  摘要：

  本文描述了一组神经酰胺类似物的合成，这些类似物探讨了酰基链的疏水性、羟基化的程度和性质。它们已被用于检测寄生原生动物酶LmjIPCS。这些研究表明，尽管C-3羟基团对酶的代谢转化不是必需的，但它提供了增强的亲和力。鉴于该酶的膜结合性质，需要一个长（C13）碳氢神经酰胺尾部以实现高亲和力和代谢转化。虽然N-酰基链也对亲和力有所贡献，但缺乏酰胺键连接的类似物在酶和细胞基础测试中作为竞争性抑制剂发挥了作用。针对这一观察结果，我们提出了一个理论模型。

  DOI：

  10.1039/c0ob00871k
• 作为试剂：
  描述：

  苯基乙烯基砜 、 N-二苯亚甲基-甘氨酸叔丁酯 在 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 、 (1S,2R,4S,5R)-2-((S)-allyloxy(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane bromide 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-tert-butyl 2-(diphenylmethyleneamino)-4-(phenylsulfonyl)butanoate 、 1,1-dimethylethyl 4-cyano-(2R)-[(diphenylmethylene)amino]-4-(phenylsulfonyl)butanoate
  参考文献：
  名称：

  通过迈克尔加成反应的谷氨酸衍生物的对映选择性溶液和固相合成

  摘要：

  在溶液中（56-89％ee）或固相（34-82％ee）上的Schiff碱酯衍生物的对映体选择性共轭加成反应，得到光学活性的非天然α-氨基酸衍生物。使用中性非离子磷腈碱，在衍生自金鸡纳生物碱的手性，非外消旋季盐存在下进行反应。

  DOI：

  10.1016/s0957-4166(01)00116-1

文献信息

• INHIBITORS OF IAP
  申请人：Cohen Frederick

  公开号：US20120202750A1

  公开（公告）日：2012-08-09

  The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: wherein X, Y, A, R 1 , R 2 , R 3 , R 4 , R 4 ′, R 5 , R 5 ′, R 6 and R 6 ′ are as described herein.

  该发明提供了新型IAP抑制剂，可用作治疗恶性肿瘤的治疗剂，其中化合物具有一般式I：其中X、Y、A、R1、R2、R3、R4、R4'、R5、R5'、R6和R6'如本文所述。
• Asymmetric synthesis of N-aryl aziridines
  作者：João Aires-de-Sousa、Sundaresan Prabhakar、Ana M. Lobo、Ana M. Rosa、Mário J.S. Gomes、Marta C. Corvo、David J. Williams、Andrew J.P. White

  DOI：10.1016/s0957-4166(01)00548-1

  日期：2002.1

  The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer's sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer's auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantio selection and a mechanism is proposed for the aziridination reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US8980837B2
  申请人：——

  公开号：US8980837B2

  公开（公告）日：2015-03-17
• Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain
  作者：John G. Mina、Jackie A. Mosely、Hayder Z. Ali、Paul W. Denny、Patrick G. Steel

  DOI：10.1039/c0ob00871k

  日期：——

  The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzymeLmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

  本文描述了一组神经酰胺类似物的合成，这些类似物探讨了酰基链的疏水性、羟基化的程度和性质。它们已被用于检测寄生原生动物酶LmjIPCS。这些研究表明，尽管C-3羟基团对酶的代谢转化不是必需的，但它提供了增强的亲和力。鉴于该酶的膜结合性质，需要一个长（C13）碳氢神经酰胺尾部以实现高亲和力和代谢转化。虽然N-酰基链也对亲和力有所贡献，但缺乏酰胺键连接的类似物在酶和细胞基础测试中作为竞争性抑制剂发挥了作用。针对这一观察结果，我们提出了一个理论模型。