5,5'-disulfanediyldipentan-1-amine | 15919-44-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: 5,5'-disulfanediyldipentan-1-amine
• 英文别名: bis-(5-amino-pentyl)-disulfide；Bis-(5-amino-pentyl)-disulfid；ε,ε'-Diamino-di-n-amyldisulfid；Bis-(ε-amino-n-amyl)-disulfid；Bis(γ-aminopentyl)disulfid；Di(ω-aminopentyl)disulfid；5-(5-Aminopentyldisulfanyl)pentan-1-amine；5-(5-aminopentyldisulfanyl)pentan-1-amine
• CAS: 15919-44-5
• 化学式: C₁₀H₂₄N₂S₂
• 分子量: 236.446
• InChiKey: PGGKETZFSZSFPL-UHFFFAOYSA-N

物化性质

• 沸点：
  352.3±27.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-disulfanediyldipentan-1-amine 、 2-hydroxyimino-3-(3-bromo-4-hydroxyphenyl)propionic acid 在 N-羟基邻苯二甲酰亚胺 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 14.0h， 以34%的产率得到(2E,2'E)-N,N-[2,2'-disulfanediylbis(pentane-5,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
  参考文献：
  名称：

  Epigenetic profiling of the antitumor natural product psammaplin A and its analogues

  摘要：

  A collection of analogues of the dimeric natural product psammaplin A that differ in the substitution on the ( halo) tyrosine aryl ring, the oxime and the diamine connection has been synthesized. The effects on cell cycle, induction of differentiation and apoptosis of the natural-product inspired series were measured on the human leukaemia U937 cell line. Epigenetic profiling included induction of p21(WAF1), effects on global H3 histone and tubulin acetylation levels as well as in vitro enzymatic assays using HDAC1, DNMT1, DNMT3A, SIRT1 and a peptide domain with p300/CBP HAT activity. Whereas the derivatives of psammaplin A with modifications in the length of the connecting chain, the oxime bond and the disulfide unit showed lower potency, the analogues with changes on the bromotyrosine ring exhibited activities comparable to those of the parent compound in the inhibition of HDAC1 and in the induction of apoptosis. The lack of HDAC1 activity of analogues modified on the disulfide bond suggests that its cleavage must occur in cells to produce the monomeric Zn2+-chelating thiol. This assumption is consistent with the molecular modelling of the complex of psammaplin A thiol with h-HDAC8. Only a weak inhibition of DNMT1, DNMT3A and residual activities with SIRT1 and a p300/CBP HAT peptide were measured for these compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.026
• 作为产物：
  描述：

  N-(5-氯戊基)苯甲酰胺 在 盐酸 、 sodium sulfide 、 sulfur 作用下， 以 乙醇 为溶剂， 生成 5,5'-disulfanediyldipentan-1-amine
  参考文献：
  名称：

  Losse,G.; Richter,K.-H., Journal fur praktische Chemie (Leipzig 1954), 1961, vol. 13, p. 23 - 29

  摘要：

  DOI：

文献信息

• SELF ASSEMBLED MOLECULES ON IMMERSION SILVER COATINGS
  申请人：Abys Joseph A.

  公开号：US20120276409A1

  公开（公告）日：2012-11-01

  A method for enhancing the corrosion resistance of an article comprising a silver coating deposited on a solderable copper substrate is provided. The method comprises exposing the copper substrate having the immersion-plated silver coating thereon to an anti-corrosion composition comprising: a) a multi-functional molecule comprising at least one organic functional group that interacts with and protects copper surfaces and at least one organic functional group that interacts with and protects silver surfaces; b) an alcohol; and c) a surfactant.

  本发明提供了一种增强银涂层在可焊接铜基底上耐腐蚀性的方法。该方法包括将浸镀银涂层的铜基底暴露在一种抗腐蚀组合物中，该组合物包括：a)一种多功能分子，其中至少包括一种有机功能基与保护铜表面相互作用并保护铜表面，以及至少包括一种有机功能基与保护银表面相互作用并保护银表面；b)一种醇；和c)一种表面活性剂。
• Method for preparing polyarylene sulfide-polyimide copolymers
  申请人：GENERAL ELECTRIC COMPANY

  公开号：EP0445588A1

  公开（公告）日：1991-09-11

  Polyarylene sulfide-polyimide copolymers are prepared by melt blending a polyarylene sulfide, preferably a polyphenylene sulfide, containing primary amino groups with a polyimide containing terminal dicarboxylate groups or functional derivatives thereof, usually anhydride groups. Curing of the polyarylene sulfide prior to reaction with the polyimide is preferred.

  聚芳基硫醚-聚酰亚胺共聚物的制备方法是将含有伯氨基的聚芳基硫醚（最好是聚苯硫醚）与含有末端二羧酸基团或其官能衍生物（通常是酸酐基团）的聚酰亚胺熔融混合。在与聚酰亚胺反应之前，最好先将聚芳基硫醚固化。
• Ratschinskii et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2998,3001,3002;engl.Ausg.S.3027,3028,3030
  作者：Ratschinskii et al.

  DOI：——

  日期：——
• Dirscherl; Weingarten, Justus Liebigs Annalen der Chemie, 1951, vol. 574, p. 131,139
  作者：Dirscherl、Weingarten

  DOI：——

  日期：——
• Indole-Derived Psammaplin A Analogues as Epigenetic Modulators with Multiple Inhibitory Activities
  作者：Raquel Pereira、Rosaria Benedetti、Santiago Pérez-Rodríguez、Angela Nebbioso、José García-Rodríguez、Vincenzo Carafa、Mayra Stuhldreier、Mariarosaria Conte、Fátima Rodríguez-Barrios、Hendrik G. Stunnenberg、Hinrich Gronemeyer、Lucia Altucci、Ángel R. de Lera

  DOI：10.1021/jm300618u

  日期：2012.11.26

  A SAR study has been carried out around a modified scaffold of the natural product psammaplin A obtained by replacing the o-bromophenol unit by an indole ring. A series of indole psammaplin A constructs were generated in a short synthetic sequence that starts with the functionalization of the C3 indole position with in situ generated nitrosoacrylate, and this is followed by protection of the beta-indole-alpha-oximinoesters, saponification, condensation with symmetrical diamines, and deprotection. Biochemical and cellular characterization using U937 and MCF-7 cells confirmed that many of these analogues displayed more potent actitivies than the parent natural product. Moreover, in addition to the reported HDAC and DNMT dual epigenetic inhibitory profile of the parent compound, some analogues, notably 4a (UVI5008), also inhibited the NAD(+)-dependent SIRT deacetylase enzymes. The SAR study provides structural insights into the mechanism of action of these multiple epigenetic ligands and paves the way for additional structural exploration to optimize their pharmacological profiles. Because of their multi(epi)target features and their action in ex vivo samples, the indole-based psammaplin A derivatives are attractive molecules for the modulation of epigenetic disorders.