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tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate | 226066-04-2

中文名称
——
中文别名
——
英文名称
tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate
英文别名
——
tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate化学式
CAS
226066-04-2
化学式
C15H19Cl2NO4S
mdl
——
分子量
380.292
InChiKey
FIQKRNPPGQDMPS-ZDUSSCGKSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    480.4±55.0 °C(Predicted)
  • 密度:
    1.367±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.8
  • 重原子数:
    23
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.53
  • 拓扑面积:
    72.1
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylateN-甲基吗啉1-羟基苯并三唑1-(3-二甲基氨基丙基)-3-乙基碳二亚胺三氟乙酸 作用下, 以 二氯甲烷 为溶剂, 生成 ethyl (S)-2-(1-((3,5-dichlorophenyl)sulfonyl)pyrrolidine-2-carboxamido)benzoate
    参考文献:
    名称:
    Highly constrained bicyclic VLA-4 antagonists
    摘要:
    VLA-4 is implicated in several inflammatory and autoimmune disease states. A series of cyclic P-amino acids (beta-aa) was studied as VLA-4 antagonists. Binding affinity was highly dependent on the dihedral angle (phi) between the amino and the carboxyl termini of the beta-aa. Compound 5m where the beta-aa is embedded in a bicycle possesses the most preferred phi (120 degrees). It is a potent and bioavailable VLA-4 antagonist (VCAM-Ig alpha 4 beta 1 IC50 = 54 nM, rat po F = 49%). (c) 2006 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2006.11.011
  • 作为产物:
    描述:
    3,5-二氯苯磺酰氯L-脯氨酸叔丁酯4-二甲氨基吡啶N,N-二异丙基乙胺 作用下, 以 二氯甲烷 为溶剂, 以94%的产率得到tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate
    参考文献:
    名称:
    The discovery of small molecule carbamates as potent dual α4β1/α4β7 integrin antagonists
    摘要:
    The alpha(4)beta(1) and alpha(4)beta(7) integrins are implicated in several inflammatory disease states. Systematic SAR studies of an alpha(4)beta(1)-specific arylsulfonyl-Pro-Tyr lead led to the identification of a new alpha(4)beta(7) binding site, best captured by O-carbamates of Tyr for this structural class. Several compounds showed a 200- to 400-fold improvement in alpha(4)beta(7) binding affinity while maintaining subnanomolar alpha(4)beta(1) activity, for example 21, VCAM-Ig alpha(4)beta(1) IC50 = 0.13 nM. VCAM-Ig alpha(4)beta(7) IC50 = 1.92 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0960-894x(01)00710-7
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文献信息

  • The discovery of small molecule carbamates as potent dual α4β1/α4β7 integrin antagonists
    作者:Linda L. Chang、Quang Truong、Richard A. Mumford、Linda A. Egger、Usha Kidambi、Kathryn Lyons、Ermengilda McCauley、Gail Van Riper、Stella Vincent、John A. Schmidt、Malcolm MacCoss、William K. Hagmann
    DOI:10.1016/s0960-894x(01)00710-7
    日期:2002.1
    The alpha(4)beta(1) and alpha(4)beta(7) integrins are implicated in several inflammatory disease states. Systematic SAR studies of an alpha(4)beta(1)-specific arylsulfonyl-Pro-Tyr lead led to the identification of a new alpha(4)beta(7) binding site, best captured by O-carbamates of Tyr for this structural class. Several compounds showed a 200- to 400-fold improvement in alpha(4)beta(7) binding affinity while maintaining subnanomolar alpha(4)beta(1) activity, for example 21, VCAM-Ig alpha(4)beta(1) IC50 = 0.13 nM. VCAM-Ig alpha(4)beta(7) IC50 = 1.92 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • Highly constrained bicyclic VLA-4 antagonists
    作者:Linda L. Chang、Quang Truong、George A. Doss、Malcolm MacCoss、Kathryn Lyons、Ermengilda McCauley、Richard Mumford、Gail Forrest、Stella Vincent、John A. Schmidt、William K. Hagmann
    DOI:10.1016/j.bmcl.2006.11.011
    日期:2007.2
    VLA-4 is implicated in several inflammatory and autoimmune disease states. A series of cyclic P-amino acids (beta-aa) was studied as VLA-4 antagonists. Binding affinity was highly dependent on the dihedral angle (phi) between the amino and the carboxyl termini of the beta-aa. Compound 5m where the beta-aa is embedded in a bicycle possesses the most preferred phi (120 degrees). It is a potent and bioavailable VLA-4 antagonist (VCAM-Ig alpha 4 beta 1 IC50 = 54 nM, rat po F = 49%). (c) 2006 Elsevier Ltd. All rights reserved.
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