4-(tritylthio)butan-1-amine | 426828-08-2

• 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: 4-(tritylthio)butan-1-amine
• 英文别名: 4-(Tritylmercapto)butylamine；4-tritylsulfanylbutan-1-amine
• CAS: 426828-08-2
• 化学式: C₂₃H₂₅NS
• 分子量: 347.524
• InChiKey: URFDSBVLFXVQNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tritylthio)butan-1-amine 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Efficient Covalent Capture of 8-Nitroguanosine via a Multiple Hydrogen-Bonded Complex

  摘要：

  A novel 1,3-diazaphenoxazine nucleoside derivative (nitroG-Grasp) bearing a thiol group with a urea linker forms multiple hydrogen-bonded complexes with 8-nitroguanosine and efficiently displaces the nitro group; thus, it is the first molecule that can covalently capture 8-nitroguanosine.

  DOI：

  10.1021/ol500452r
• 作为产物：
  描述：

  2-(4-(tritylthio)butyl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以86%的产率得到4-(tritylthio)butan-1-amine
  参考文献：
  名称：

  氧化还原活性磁共振成像造影剂：含硫醇的 1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸衍生物的研究

  摘要：

  具有三到九个碳的硫醇封端烷基侧链的同源系列 1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸钆 (III) 配合物的合成和构效关系报告长度。观察到的具有 C-3 至 C-7 侧链长度的化合物与人血清白蛋白 (HSA) 的结合被同型半胱氨酸以与单位点结合一致的方式抑制。观察到的具有 C-8 和 C-9 侧链长度的化合物与 HSA 的结合仅部分被同型半胱氨酸抑制，与多位点结合一致。C-7 化合物的结合亲和力可能与 HSA 氧化态有关。二维1 H– 1H NMR TOCSY 提供了 C-6 化合物的铕类似物与 HSA-Cys 34共价结合的证据。钆复合物在 7 T 时的纵向水-质子 MRI 弛豫度在与 HSA 结合后增加。基于这些结果，C-6 和 C-7 化合物被确定为有前途的氧化还原敏感 MRI 造影剂。

  DOI：

  10.1021/jm300736f

文献信息

• Structure–Activity Relationship of <i>S</i>-Trityl-<scp>l</scp>-Cysteine Analogues as Inhibitors of the Human Mitotic Kinesin Eg5
  作者：Salvatore DeBonis、Dimitrios A. Skoufias、Rose-Laure Indorato、François Liger、Bernard Marquet、Christian Laggner、Benoît Joseph、Frank Kozielski

  DOI：10.1021/jm070606z

  日期：2008.3.13

  The human kinesin Eg5 is a potential drug target for cancer chemotherapy. Eg5 specific inhibitors cause cells to block in mitosis with a characteristic monoastral spindle phenotype. Prolonged metaphase block eventually leads to apoptotic cell death. S-trityl-L-cysteine (STLC) is a tight-binding inhibitor of Eg5 that prevents mitotic progression. It has proven antitumor activity as shown in the NCI 60 tumor cell line screen. It is of considerable interest to define the minimum chemical structure that is essential for Eg5 inhibition and to develop more potent STLC analogues. An initial structure-activity relationship study on a series of STLC analogues reveals the minimal skeleton necessary for Eg5 inhibition as well as indications of how to obtain more potent analogues. The most effective compounds investigated with substitutions at the paraposition of one phenyl ring have an estimated K-i(app) of 100 nM in vitro and induce mitotic arrest with an EC50 of 200 nM.
• Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2<i>H</i>-indazoles
  作者：Kelli M. Farber、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/jo501014e

  日期：2014.8.1

  Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1 degrees-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl) (tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.
• [EN] ASYMMETRIC PIPERAZINE-BASED CATIONIC LIPIDS<br/>[FR] LIPIDES CATIONIQUES À BASE DE PIPÉRAZINE ASYMÉTRIQUE
  申请人：[en]TRANSLATE BIO, INC.

  公开号：WO2023178167A1

  公开（公告）日：2023-09-21

  The present invention provides, in part, asymmetric piperazine-based lipid compounds of Formula (I'), and sub-formulas thereof or a pharmaceutically acceptable salt thereof. The compounds provided herein can be useful for delivery and expression of mRNA and encoded protein, e.g., as a component of liposomal delivery vehicle, and accordingly can be useful for treating various diseases, disorders and conditions, such as those associated with deficiency of one or more proteins.
• Redox-active Magnetic Resonance Imaging Contrast Agents: Studies with Thiol-bearing 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetracetic Acid Derivatives
  作者：Bhumasamudram Jagadish、Gerald P. Guntle、Dezheng Zhao、Vijay Gokhale、Tarik J. Ozumerzifon、Ali M. Ahad、Eugene A. Mash、Natarajan Raghunand

  DOI：10.1021/jm300736f

  日期：2012.12.13

  The synthesis and structure–activity relationships of a homologous series of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid gadolinium(III) complexes bearing thiol-terminated alkyl side chains from three to nine carbons in length are reported. The observed binding with human serum albumin (HSA) of the compounds having C-3 through C-7 side chain lengths was inhibited by homocysteine in a manner

  具有三到九个碳的硫醇封端烷基侧链的同源系列 1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸钆 (III) 配合物的合成和构效关系报告长度。观察到的具有 C-3 至 C-7 侧链长度的化合物与人血清白蛋白 (HSA) 的结合被同型半胱氨酸以与单位点结合一致的方式抑制。观察到的具有 C-8 和 C-9 侧链长度的化合物与 HSA 的结合仅部分被同型半胱氨酸抑制，与多位点结合一致。C-7 化合物的结合亲和力可能与 HSA 氧化态有关。二维1 H– 1H NMR TOCSY 提供了 C-6 化合物的铕类似物与 HSA-Cys 34共价结合的证据。钆复合物在 7 T 时的纵向水-质子 MRI 弛豫度在与 HSA 结合后增加。基于这些结果，C-6 和 C-7 化合物被确定为有前途的氧化还原敏感 MRI 造影剂。
• Efficient Covalent Capture of 8-Nitroguanosine <i>via</i> a Multiple Hydrogen-Bonded Complex
  作者：Yasufumi Fuchi、Shigeki Sasaki

  DOI：10.1021/ol500452r

  日期：2014.3.21

  A novel 1,3-diazaphenoxazine nucleoside derivative (nitroG-Grasp) bearing a thiol group with a urea linker forms multiple hydrogen-bonded complexes with 8-nitroguanosine and efficiently displaces the nitro group; thus, it is the first molecule that can covalently capture 8-nitroguanosine.