S-(4-isopropylbenzyl)isothiourea hydrobromide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: S-(4-isopropylbenzyl)isothiourea hydrobromide
• 英文别名: (4-propan-2-ylphenyl)methyl carbamimidothioate;hydrobromide
• 化学式: BrH*C₁₁H₁₆N₂S
• 分子量: 289.239
• InChiKey: UHEAJXLVIXWYHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-(4-isopropylbenzyl)isothiourea hydrobromide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 p-cymen-7-thiol
  参考文献：
  名称：

  Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus

  摘要：

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.

  DOI：

  10.1021/jm070564e
• 作为产物：
  描述：

  对异丙基溴苄 、 硫脲 以 乙醇 为溶剂， 反应 5.0h， 以97%的产率得到S-(4-isopropylbenzyl)isothiourea hydrobromide
  参考文献：
  名称：

  S-Benzylisothiourea derivatives as small-molecule inhibitors of indoleamine-2,3-dioxygenase

  摘要：

  S-Benzylisothiourea 3a was discovered by its ability to inhibit indoleamine-2,3-dioxygenase (IDO) in our screening program. Subsequent optimization of the initial hit 3a lead to the identification of sub-mu M inhibitors 3r and 10h, both of which suppressed kynurenine production in A431 cells. Synthesis and structure-activity relationship of S-benzylisothiourea analogues as small-molecule inhibitors of IDO are described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.025

文献信息

• Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus
  作者：Hui Xie、Danny Ng、Sergey N. Savinov、Barna Dey、Peter D. Kwong、Richard Wyatt、Amos B. Smith、Wayne A. Hendrickson

  DOI：10.1021/jm070564e

  日期：2007.10.1

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.
• S-Benzylisothiourea derivatives as small-molecule inhibitors of indoleamine-2,3-dioxygenase
  作者：Kenji Matsuno、Kazushige Takai、Yoshinobu Isaka、Yuka Unno、Masayuki Sato、Osamu Takikawa、Akira Asai

  DOI：10.1016/j.bmcl.2010.07.025

  日期：2010.9

  S-Benzylisothiourea 3a was discovered by its ability to inhibit indoleamine-2,3-dioxygenase (IDO) in our screening program. Subsequent optimization of the initial hit 3a lead to the identification of sub-mu M inhibitors 3r and 10h, both of which suppressed kynurenine production in A431 cells. Synthesis and structure-activity relationship of S-benzylisothiourea analogues as small-molecule inhibitors of IDO are described. (C) 2010 Elsevier Ltd. All rights reserved.