S-(5-bromopentyl)methanesulfonothioate | 212262-06-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: S-(5-bromopentyl)methanesulfonothioate
• 英文别名: 5-bromopentyl methanethiosulfonate；1-Bromo-5-methylsulfonylsulfanylpentane
• CAS: 212262-06-1
• 化学式: C₆H₁₃BrO₂S₂
• 分子量: 261.204
• InChiKey: QNKMONRUAPQHLA-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±25.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(5-bromopentyl)methanesulfonothioate 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 (E)-S-(5-(3-(2,4-dichlorophenyl)-N-hydroxyacrylamido)pentyl)methanesulfonothioate
  参考文献：
  名称：

  Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

  摘要：

  Botulinum neurotoxins have remarkable persistence (similar to weeks to months in cells), outlasting the small-molecule inhibitors designed to target them. To address this disconnect, inhibitors bearing two pharmacophores.a zinc binding group and a Cys-reactive warhead.were designed to leverage both affinity and reactivity. A series of first-generation bifunctional inhibitors was achieved through structure-based inhibitor design. Through X-ray crystallography, engagement of both the catalytic Zn2+ and Cys165 was confirmed. A second-generation series improved on affinity by incorporating known reversible inhibitor pharmacophores; the mechanism was confirmed by exhaustive dialysis, mass spectrometry, and in vitro evaluation against the C165S mutant. Finally, a third-generation inhibitor was shown to have good cellular activity and low toxicity. In addition to our findings, an alternative method of modeling time-dependent inhibition that simplifies assay setup and allows comparison of inhibition models is discussed.

  DOI：

  10.1021/acs.jmedchem.0c01006
• 作为产物：
  描述：

  1,5-二溴戊烷 、 硫甲磺酸钠 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以66%的产率得到S-(5-bromopentyl)methanesulfonothioate
  参考文献：
  名称：

  Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A

  摘要：

  Botulinum neurotoxins have remarkable persistence (similar to weeks to months in cells), outlasting the small-molecule inhibitors designed to target them. To address this disconnect, inhibitors bearing two pharmacophores.a zinc binding group and a Cys-reactive warhead.were designed to leverage both affinity and reactivity. A series of first-generation bifunctional inhibitors was achieved through structure-based inhibitor design. Through X-ray crystallography, engagement of both the catalytic Zn2+ and Cys165 was confirmed. A second-generation series improved on affinity by incorporating known reversible inhibitor pharmacophores; the mechanism was confirmed by exhaustive dialysis, mass spectrometry, and in vitro evaluation against the C165S mutant. Finally, a third-generation inhibitor was shown to have good cellular activity and low toxicity. In addition to our findings, an alternative method of modeling time-dependent inhibition that simplifies assay setup and allows comparison of inhibition models is discussed.

  DOI：

  10.1021/acs.jmedchem.0c01006

文献信息

• Site-specific drug delivery
  申请人：Dime S. David

  公开号：US20060009375A1

  公开（公告）日：2006-01-12

  Compounds and methods which are useful for the site-specific delivery and localization of drugs are provided. The compounds can be represented by the formula: A-L-D wherein A is an anchoring moiety; L is a linking group; and D is a drug.

  本发明提供了用于特定部位输送和定位药物的化合物和方法。这些化合物可以用公式A-L-D表示，其中A是锚定基团；L是连接基团；D是药物。
• SITE-SPECIFIC DRUG DELIVERY
  申请人：Dime, David S.

  公开号：EP0966304B1

  公开（公告）日：2005-05-25
• US7033765B1
  申请人：——

  公开号：US7033765B1

  公开（公告）日：2006-04-25
• [EN] SITE-SPECIFIC DRUG DELIVERY<br/>[FR] ADMINISTRATION DE MEDICAMENT A SPECIFICITE DE SITE
  申请人：——

  公开号：WO1998036777A1

  公开（公告）日：1998-08-27

  [EN] Compounds and methods which are useful for the site-specific delivery and localization of drugs are provided. The compounds can be represented by the formula: A-L-D wherein A is an anchoring moiety; L is a linking group; and D is a drug.
  [FR] L'invention a trait à des composés et aux méthodes afférentes se révélant des plus utiles en matière d'administration de médicaments à spécificité de site et de localisation de ceux-ci. Ces composés peuvent être représentés par la formule A-L-D dans laquelle A représente une fraction d'ancrage, L, un groupe de liaison et D, le médicament.
• Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A
  作者：Lucy Lin、Margaret E. Olson、Takashi Sugane、Lewis D. Turner、Margarita A. Tararina、Alexander L. Nielsen、Elbek K. Kurbanov、Sabine Pellett、Eric A. Johnson、Seth M. Cohen、Karen N. Allen、Kim D. Janda

  DOI：10.1021/acs.jmedchem.0c01006

  日期：2020.10.8

  Botulinum neurotoxins have remarkable persistence (similar to weeks to months in cells), outlasting the small-molecule inhibitors designed to target them. To address this disconnect, inhibitors bearing two pharmacophores.a zinc binding group and a Cys-reactive warhead.were designed to leverage both affinity and reactivity. A series of first-generation bifunctional inhibitors was achieved through structure-based inhibitor design. Through X-ray crystallography, engagement of both the catalytic Zn2+ and Cys165 was confirmed. A second-generation series improved on affinity by incorporating known reversible inhibitor pharmacophores; the mechanism was confirmed by exhaustive dialysis, mass spectrometry, and in vitro evaluation against the C165S mutant. Finally, a third-generation inhibitor was shown to have good cellular activity and low toxicity. In addition to our findings, an alternative method of modeling time-dependent inhibition that simplifies assay setup and allows comparison of inhibition models is discussed.