(2R,3S,4R)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile | 1393809-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4R)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile
• 英文别名: (2R,3S,4R)-1-allyl-3-(4-bromophenyl)-4-((trityloxy)methyl)azetidine-2-carbonitrile；(2R,3S,4R)-3-(4-bromophenyl)-1-prop-2-enyl-4-(trityloxymethyl)azetidine-2-carbonitrile
• CAS: 1393809-88-5
• 化学式: C₃₃H₂₉BrN₂O
• 分子量: 549.51
• InChiKey: OXPKMQJBKUIYSR-CPCREDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile 在 咪唑 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 26.75h， 生成 (2S,3R,4R)-1-allyl-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-4-(hydroxymethyl)azetidine-2-carbonitrile
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF CRYPTOSPORIDIOSIS
  [FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE LA CRYPTOSPORIDIOSE

  摘要：

  隐孢子虫是导致幼儿早逝的主要原因之一，对这种重要传染病的完全有效治疗方法尚缺乏。一种双环氮杂环丙烷化合物系列被披露，对所有经过测试的隐孢子虫C. parvum分离株具有强大的体外活性，在C. hominis和C. parvum之间具有可比较的效力，并且通过每日一次的给药方案治愈了高度易感的免疫抑制小鼠体内的隐孢子虫病。

  公开号：

  WO2021081315A1
• 作为产物：
  描述：

  2-(allyl((1R,2S)-1-(4-bromophenyl)-1-chloro-3-(trityloxy)propan-2-yl)amino)acetonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以46%的产率得到(2R,3S,4R)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile
  参考文献：
  名称：

  Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-like Libraries

  摘要：

  The synthesis and diversification of a densely functionalized azetidine ring system to gain access to a wide variety of fused, bridged, and spirocyclic ring systems is described. The in vitro physicochemical and pharmacokinetic properties of representative library members are measured in order to evaluate the use of these scaffolds for the generation of lead-like molecules to be used in targeting the central nervous system. The solid-phase synthesis of a 1976-membered library of spirocyclic azetidines is also described.

  DOI：

  10.1021/jo300974j

文献信息

• Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-like Libraries
  作者：Jason T. Lowe、Maurice D. Lee、Lakshmi B. Akella、Emeline Davoine、Etienne J. Donckele、Landon Durak、Jeremy R. Duvall、Baudouin Gerard、Edward B. Holson、Adrien Joliton、Sarathy Kesavan、Berenice C. Lemercier、Haibo Liu、Jean-Charles Marié、Carol A. Mulrooney、Giovanni Muncipinto、Morgan Welzel-O’Shea、Laura M. Panko、Ann Rowley、Byung-Chul Suh、Meryl Thomas、Florence F. Wagner、Jingqiang Wei、Michael A. Foley、Lisa A. Marcaurelle

  DOI：10.1021/jo300974j

  日期：2012.9.7

  The synthesis and diversification of a densely functionalized azetidine ring system to gain access to a wide variety of fused, bridged, and spirocyclic ring systems is described. The in vitro physicochemical and pharmacokinetic properties of representative library members are measured in order to evaluate the use of these scaffolds for the generation of lead-like molecules to be used in targeting the central nervous system. The solid-phase synthesis of a 1976-membered library of spirocyclic azetidines is also described.
• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF CRYPTOSPORIDIOSIS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE LA CRYPTOSPORIDIOSE
  申请人：BROAD INST INC

  公开号：WO2021081315A1

  公开（公告）日：2021-04-29

  Cryptosporidium is a leading contributor to early childhood mortality, and fully effective treatment for this important infectious disease is lacking. A bicyclic azetidine compound series is disclosed having potent in vitro activity against all C. parvum isolates tested, comparable potencies against C. hominis and C. parvum, and cured cryptosporidiosis in highly susceptible immunosuppressed mice with once-daily dosing.

  隐孢子虫是导致幼儿早逝的主要原因之一，对这种重要传染病的完全有效治疗方法尚缺乏。一种双环氮杂环丙烷化合物系列被披露，对所有经过测试的隐孢子虫C. parvum分离株具有强大的体外活性，在C. hominis和C. parvum之间具有可比较的效力，并且通过每日一次的给药方案治愈了高度易感的免疫抑制小鼠体内的隐孢子虫病。