(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate
• 英文别名: (R)-2-amino-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol benzoic acid salt；(R)-2-amino-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol benzoate；(2R)-2-amino-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol;benzoic acid
• 化学式: C₇H₆O₂*C₇H₁₅NO₃
• 分子量: 283.324
• InChiKey: AUUVEWSRUXIGSP-KGZKBUQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate 在 吡啶 、 盐酸 、 氢氧化钾 、 sodium hydroxide 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 19.75h， 生成 benzyl N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylsulfanylbutan-2-yl]carbamate
  参考文献：
  名称：

  （1S）-1-[（（4R）-2,2-二甲基-1,3-二氧戊环+ -4-基] [-2-羟乙基氨基苯甲酸鎓]，手性2-氨基链烷醇的通用结构单元：简明合成及其应用奈非那韦，一种有效的HIV蛋白酶抑制剂。

  摘要：

  简明合成2-氨基链烷醇，（1S）-1-[（（4R）-2,2-二甲基-1,3-二氧戊环-4-基] -2-羟乙基苯甲酸铵（1a）的通用手性C4结构单元），进行了描述。1（1a及其对映异构体1b）充当光学活性的2-氨基-1,3,4-丁三醇的四个立体异构体。通过将其应用于实用的有效的HIV蛋白酶抑制剂奈非那韦（2）的合成以及三个3的非对映异构体的立体定向合成，证明了1的多功能性。

  DOI：

  10.1021/jo991793e
• 作为产物：
  描述：

  4,4-二甲基-3,5,8-三氧杂双环[5,1,0]辛烷 在 palladium on activated charcoal 甲烷磺酸 、 氢气 作用下， 以 异丙醇 、 丙酮 为溶剂， 40.0 ℃ 、1.5 MPa 条件下， 反应 40.0h， 生成 (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate
  参考文献：
  名称：

  WO2008/30118

  摘要：

  公开号：

文献信息

• ACYCLIC AMINE INHIBITORS OF 5-METHYTIOADENOSINE PHOSPHORYLASE AND NUCLEOSIDASE
  申请人：Clinch Keith

  公开号：US20110046167A1

  公开（公告）日：2011-02-24

  The present invention relates to compounds of the general formula (I) which are inhibitors of 5′-methylthioadenosine phosphorylase or 5′-methylthioadenosine nucleosidase. The invention also relates to the use of these compounds in the treatment of diseases or conditions in which it is desirable to inhibit 5′-methylthioadenosine phosphorylase or 5′-methylthioadenosine nucleosidase including cancer, and to pharmaceutical compositions containing the compounds.

  本发明涉及一般公式（I）的化合物，它们是5'-甲基硫腺苷磷酸化酶或5'-甲基硫腺苷核苷酸酶的抑制剂。本发明还涉及使用这些化合物治疗希望抑制5'-甲基硫腺苷磷酸化酶或5'-甲基硫腺苷核苷酶的疾病或病况，包括癌症，并且涉及含有这些化合物的药物组合物。
• Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics
  作者：Keith Clinch、Gary B. Evans、Richard F.G. Fröhlich、Shivali A. Gulab、Jemy A. Gutierrez、Jennifer M. Mason、Vern L. Schramm、Peter C. Tyler、Anthony D. Woolhouse

  DOI：10.1016/j.bmc.2012.07.006

  日期：2012.9

  Several acyclic hydroxy-methylthio-amines with 3-5 carbon atoms were prepared and coupled via a methylene link to 9-deazaadenine. The products were tested for inhibition against human MTAP and Escherichia coli and Neisseria meningitidis MTANs and gave K-i values as low as 0.23 nM. These results were compared to those obtained with 1st and 2nd generation inhibitors (1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol (MT-Immucillin-A, 3) and (3R,4S)-1-[9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine (MT-DADMe-Immucillin-A, 4). The best inhibitors were found to exhibit binding affinities of approximately 2- to 4-fold those of 3 but were significantly weaker than 4. Cleavage of the 2,3 carbon-carbon bond in MT-Immucillin-A (3) gave an acyclic product (79) with a 21,500 fold loss of activity against E. coli MTAN. In another case, N-methylation of a side chain secondary amine resulted in a 250-fold loss of activity against the same enzyme [(+/-)-65 vs (+/-)-68]. The inhibition results were also contrasted with those acyclic derivatives previously prepared as inhibitors for a related enzyme, purine nucleoside phosphorylase (PNP), where some inhibitors in the latter case were found to be more potent than their cyclic counterparts. (C) 2012 Elsevier Ltd. All rights reserved.
• WO2008/30119
  申请人：——

  公开号：——

  公开（公告）日：——
• ACYCLIC AMINE INHIBITORS OF 5'-METHYLTHIOADENOSINE PHOSPHORYLASE AND NUCLEOSIDASE
  申请人：Callaghan Innovation Research Limited

  公开号：EP2049543B1

  公开（公告）日：2014-11-05
• US8383636B2
  申请人：——

  公开号：US8383636B2

  公开（公告）日：2013-02-26