3-(1-(5-(3-hydroxy-2-thioxopyridin-1(2H)-yl)pentyl)-1H-1,2,3-triazol-4-yl)benzonitrile | 1416915-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1-(5-(3-hydroxy-2-thioxopyridin-1(2H)-yl)pentyl)-1H-1,2,3-triazol-4-yl)benzonitrile
• 英文别名: 3-[1-[5-(3-Hydroxy-2-sulfanylidenepyridin-1-yl)pentyl]triazol-4-yl]benzonitrile；3-[1-[5-(3-hydroxy-2-sulfanylidenepyridin-1-yl)pentyl]triazol-4-yl]benzonitrile
• CAS: 1416915-72-4
• 化学式: C₁₉H₁₉N₅OS
• 分子量: 365.459
• InChiKey: QQYCFXUASOHQCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-叠氮戊醇,5-AZIDO-1-PENTANOL 在 劳森试剂 、 copper(l) iodide 、 三溴化硼 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 115.0h， 生成 3-(1-(5-(3-hydroxy-2-thioxopyridin-1(2H)-yl)pentyl)-1H-1,2,3-triazol-4-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship of 3-Hydroxypyridine-2-thione-Based Histone Deacetylase Inhibitors

  摘要：

  We previously identified 3-hydroxypyridine-2-thione (3HPT) as a novel zinc binding group for histone deacetylase (HDAC) inhibition. Early structure activity relationship (SAR) studies led to various small molecules possessing selective inhibitory activity against HDAC6 or HDAC8 but devoid of HDAC1 inhibition. To delineate further the depth of the SAR of 3HPT-derived HDAC inhibitors (HDACi), we have extended the SAR studies to include the linker region and the surface recognition group to optimize the HDAC inhibition. The current efforts resulted in the identification of two lead compounds, 10d and 14e, with potent HDAC6 and HDAC8 activities that are inactive against HDAC1. These new HDACi possess anticancer activities against various cancer cell lines including Jurkat J.gamma 1 for which SAHA and the previously disclosed 3HPT-derived HDACi were inactive.

  DOI：

  10.1021/jm401225q

文献信息

• NON-PEPTIDE MACROCYCLIC HISTONE DEACETYLASE (HDAC) INHIBITORS AND METHODS OF MAKING AND USING THEREOF
  申请人：Oyelere Adegboyega

  公开号：US20120329741A1

  公开（公告）日：2012-12-27

  Compounds of Formula I or II, and methods of making and using thereof, are described herein. M represents a macrolide subunit, E is a C 1-6 group, optionally containing one or more heteroatoms, D is an alkyl or aryl group, A is a linking group connected to D, B is an alkyl, alkylaryl or alkylheteroaryl spacer group, ZBG is a Zinc Binding Group, R 1 , R 2 and R 4 are independently are selected from hydrogen, a C1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 1-6 alkanoate group, a C 2-6 carbamate group, a C 2-6 carbonate group, a C 2-6 carbamate group, or a C 2-6 thiocarbamate group, R 3 is hydrogen or —OR 5 , R 5 is selected from a group consisting of Hydrogen, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, C 1-6 alkanoate group, C 2-6 carbamate group, C 2-6 carbonate group, C 2-6 carbamate group, or C 2-6 thiocarbamate group.

  本文描述了I或II式化合物及其制备和使用方法。其中，M代表大环内酯亚基，E为C1-6基团，可选含有一个或多个杂原子，D为烷基或芳基基团，A为连接到D的连接基团，B为烷基、烷基芳基或烷基杂芳基间隔基团，ZBG为锌结合基团，R1、R2和R4独立地选择自氢、C1-6烷基、C2-6烯基、C2-6炔基、C1-6烷酸酯基、C2-6氨基甲酸酯基、C2-6碳酸酯基、C2-6氨基甲酰基或C2-6硫代氨基甲酰基，R3为氢或-OR5，R5选择自氢、C1-6烷基、C2-6烯基、C2-6炔基、C1-6烷酸酯基、C2-6氨基甲酸酯基、C2-6碳酸酯基、C2-6氨基甲酰基或C2-6硫代氨基甲酰基。
• US8871728B2
  申请人：——

  公开号：US8871728B2

  公开（公告）日：2014-10-28