2-benzothiazolyl 2-methanesulfonoxyethyl disulfide | 183056-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-benzothiazolyl 2-methanesulfonoxyethyl disulfide
• 英文别名: 2-(1,3-Benzothiazol-2-yldisulfanyl)ethyl methanesulfonate
• CAS: 183056-94-2
• 化学式: C₁₀H₁₁NO₃S₄
• 分子量: 321.466
• InChiKey: ONHGLFMUKWLVCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  异戊胺 、 Fmoc-L-苯丙氨酸 、 2-benzothiazolyl 2-methanesulfonoxyethyl disulfide 、 (S)-2-bromo-4-(tert-butoxy)-4-oxobutanoic acid 生成 2-[(2S,5S)-5-benzyl-7-(3-methylbutyl)-3,6-dioxo-1,4,7-thiadiazonan-2-yl]acetic acid
  参考文献：
  名称：

  Novel inhibitors of α4β1 integrin receptor interactions through library synthesis and screening

  摘要：

  A library of 2302 small molecule beta-turn mimetics was screened for inhibition of the alpha 4 beta 1 integrin-CS1 splice variant binding interaction. Preliminary data revealed several active ligands, and validation with purified material culminated in the identification of some of the first small molecule ligands (1, IC50 = 5 mu M, and 2, IC50 = 8 mu M) to be reported for this class of integrins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00416-8
• 作为产物：
  描述：

  二硫化二苯并噻唑 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.3h， 生成 2-benzothiazolyl 2-methanesulfonoxyethyl disulfide
  参考文献：
  名称：

  通过β-转角模拟文库的合成和筛选鉴定生长抑素受体亚型 5 的强杂环配体

  摘要：

  描述了平行合成中环杂环 β-转角模拟物 (1) 的方法，它能够快速制备模拟物库，用于识别受体的小分子配体。这种方法的通用性首先通过模拟物 1a-g 的快速和高产合成来证明，该模拟物显示出广泛的蛋白质氨基酸侧链。然后通过基于在生长抑素转角区域中发现的关键 Trp-Lys 基序合成一个聚焦的 β-转角模拟物库来鉴定具有药用价值的肽生长抑素的小分子杂环模拟物。针对一组五种克隆的人类生长抑素受体 (hSST1-hSST5) 筛选文库，鉴定出一种对 hSST5 具有选择性的有效小分子配体 (1h)，以及针对受体亚型 1-4 的有效配体。此外，结构-活性关系被用来确定三种多样性输入中每一种的重要性……

  DOI：

  10.1021/ja983742p

文献信息

• Expedient solid-phase synthesis of putative β-turn mimetics incorporating the i + 1, i + 2, and i + 3 sidechains
  作者：Alex A. Virgilio、Stephan C. Schürer、Jonathan A. Ellman

  DOI：10.1016/0040-4039(96)01572-9

  日期：1996.9

  number of putative β-turn mimetics that incorporate sidechain functionality at the i + 1, i + 2, and i + 3 positions were synthesized on solid support in high levels of purity and in good overall yields from readily available starting materials. A variety of sidechain functionality, ring sizes, and sidechain stereochemistries were introduced demonstrating the generality of the synthesis method. A significant

  从固体原料上以高水平的纯度和良好的总收率从容易获得的起始原料合成了许多在i + 1，i + 2和i + 3位置结合了侧链功能的推定的β-turn模拟物。引入了各种侧链功能，环大小和侧链立体化学，证明了合成方法的一般性。合成顺序的一个重要特征是使用了一种胍树脂，该胍树脂既可以用作固相萃取树脂，也可以用作与载体结合的通用碱催化剂。
• Compounds That Activate the Mouse Melanocortin-1 Receptor Identified by Screening a Small Molecule Library Based upon the β-Turn
  作者：Carrie Haskell-Luevano、Åsa Rosenquist、Andrew Souers、Kathy C. Khong、Jonathon A. Ellman、Roger D. Cone

  DOI：10.1021/jm990190s

  日期：1999.10.1

  A library of 951 compounds based upon the beta-turn motif were examined for their ability to stimulate the melanocortin-1 receptor. From this screening process, we have identified two compounds possessing low micromolar agonist activity at the mMC1R. The compound EL1 with racemic Nal(2') in the i + 1 position, DPro in the i + 2 position, and Trp in the i + 3 position possesses an EC50 Of 42.5 +/- 6.9 mu M. Compound EL2 with Trp in the i + 1 position, DLys in the i + 2 position, and Phe in the i + 3 position possesses an EC50 value of 63.4 +/- 26.9 mu M. The results of the library screening process are consistent with a hypothesis dating back to the 1980s proposing that a beta-turn conformation involving the melanocortin "Phe-Arg-Trp" core amino acids provides the key recognition element. Additionally, these compounds represent the first nonpeptidic heterocyclic molecules reported to date that are able to activate the MC1R, a melanocyte receptor involved in skin pigmentation and animal coat coloration.