N-[[(2R,3R,4S)-1-allyl-3-(4-bromophenyl)-4-(trityloxymethyl)azetidin-2-yl]methyl] -2-nitrobenzenesulfonamide | 1393809-94-3

• 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: N-[[(2R,3R,4S)-1-allyl-3-(4-bromophenyl)-4-(trityloxymethyl)azetidin-2-yl]methyl] -2-nitrobenzenesulfonamide
• 英文别名: N-[[(2R,3R,4S)-3-(4-bromophenyl)-1-prop-2-enyl-4-(trityloxymethyl)azetidin-2-yl]methyl]-2-nitrobenzenesulfonamide
• CAS: 1393809-94-3
• 化学式: C₃₉H₃₆BrN₃O₅S
• 分子量: 738.702
• InChiKey: AGPZGMMUKSQBNY-QOZRZDGHSA-N

物化性质

• 沸点：
  788.2±70.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[[(2R,3R,4S)-1-allyl-3-(4-bromophenyl)-4-(trityloxymethyl)azetidin-2-yl]methyl] -2-nitrobenzenesulfonamide 在 Grubbs catalyst first generation 、 偶氮二异丁腈 、 2-硝基苯磺酰肼 、 三丁基氯化锡 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 苯硫酚 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 苯 为溶剂， 反应 34.67h， 生成 [(8R,9R,10S)-6-methyl-9-phenyl-1,6-diazabicyclo[6.2.0]decan-10-yl]methanol
  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
• 作为产物：
  描述：

  (1R,2R)-1-(4-bromophenyl)-2-(prop-2-enylamino)propane-1,3-diol 在 吡啶 、 2,6-二甲基吡啶 、 氯化亚砜 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.67h， 生成 N-[[(2R,3R,4S)-1-allyl-3-(4-bromophenyl)-4-(trityloxymethyl)azetidin-2-yl]methyl] -2-nitrobenzenesulfonamide
  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

• [EN] COMPOUNDS AND METHODS FOR THE TREATMENT OF PARASITIC DISEASES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE MALADIES PARASITAIRES
  申请人：BROAD INST INC

  公开号：WO2018175385A1

  公开（公告）日：2018-09-27

  Provided herein are compounds useful for the treatment of various parasitic diseases. These compounds, as well as pharmaceutically acceptable salts thereof may be formulated in pharmaceutical compostions, veterinary compositions and may be used in methods of treatment and/or prophylaxis of diseases spread by parasites, including malaria and cryptosporidiosis.

  本文提供了用于治疗各种寄生虫病的化合物。这些化合物以及其药用盐可以制成药物组合物、兽医组合物，并可用于治疗和/或预防由寄生虫传播的疾病，包括疟疾和隐孢子虫病。
• Compounds and methods for the treatment of parasitic diseases
  申请人：THE BROAD INSTITUTE, INC.

  公开号：US11174260B2

  公开（公告）日：2021-11-16

  Provided herein are compounds useful for the treatment of various parasitic diseases. These compounds, as well as pharmaceutically acceptable salts thereof may be formulated in pharmaceutical compostions, veterinary compositions and may be used in methods of treatment and/or prophylaxis of diseases spread by parasites, including malaria and cryptosporidiosis.

  本文提供的化合物可用于治疗各种寄生虫病。这些化合物及其药学上可接受的盐类可配制成药物组合物、兽药组合物，并可用于治疗和/或预防由寄生虫传播的疾病，包括疟疾和隐孢子虫病。
• COMPOUNDS AND METHODS FOR THE TREATMENT OF MALARIA
  申请人：THE BROAD INSTITUTE, INC.

  公开号：US20160289235A1

  公开（公告）日：2016-10-06

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of malaria.
• COMPOUNDS AND METHODS FOR THE TREATMENT OF PARASITIC DISEASES
  申请人：THE BROAD INSTITUTE, INC.

  公开号：US20200095253A1

  公开（公告）日：2020-03-26

  Provided herein are compounds useful for the treatment of various parasitic diseases. These compounds, as well as pharmaceutically acceptable salts thereof may be formulated in pharmaceutical compostions, veterinary compositions and may be used in methods of treatment and/or prophylaxis of diseases spread by parasites, including malaria and cryptosporidiosis.
• 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.