N¹-hydroxy-N⁸-(4-nitrophenyl)octanediamid | 149647-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N¹-hydroxy-N⁸-(4-nitrophenyl)octanediamid
• 英文别名: N'-hydroxy-N-(4-nitrophenyl)octanediamide
• CAS: 149647-99-4
• 化学式: C₁₄H₁₉N₃O₅
• 分子量: 309.322
• InChiKey: WHMZMGZSZMTARN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-(4-nitro-phenylcarbamoyl)-heptanoic acid 在 4-二甲氨基吡啶 、 ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate 、 N,N-二异丙基乙胺 、 盐酸羟胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以74%的产率得到N¹-hydroxy-N⁸-(4-nitrophenyl)octanediamid
  参考文献：
  名称：

  使用2-（叔丁氧基羰基氧基亚氨基）-2-氰基乙酸乙酯在固相支持物上进行无消旋的较长N端肽异羟肟酸酯合成

  摘要：

  在室温下，在DIPEA / DMAP存在下，由2-（叔丁氧基羰基氧基亚氨基）-2-氰基乙酸乙酯直接从羧酸/氨基酸直接合成肽异羟肟酸的简便，高效，无消旋，环境友好的方案是描述。该方法与基于Fmoc的固相肽合成（SPPS）的兼容性还通过在树脂上合成三种相对较大的N端肽异羟肟酸来证明。同样，一些生物学上重要的异羟肟酸酯是使用该方案合成的。

  DOI：

  10.1016/j.tetlet.2015.09.084

文献信息

• Modified Cap Group Suberoylanilide Hydroxamic Acid Histone Deacetylase Inhibitor Derivatives Reveal Improved Selective Antileukemic Activity
  作者：Chanaz Salmi-Smail、Aurélie Fabre、Franck Dequiedt、Audrey Restouin、Rémy Castellano、Slaveia Garbit、Philippe Roche、Xavier Morelli、Jean Michel Brunel、Yves Collette

  DOI：10.1021/jm901358y

  日期：2010.4.22

  A series of SAHA cap derivatives was designed and prepared in good-to-excellent yields that varied from 49% to 95%. These derivatives were evaluated for their antiproliferative activity in several human cancer cell lines. Antiproliferative activity was observed for concentrations varying from 0.12 to > 100 mu M, and a molecular modeling approach of selected SAHA derivatives, based on available structural information of human HDAC8 in complex with SAHA, was performed. Strikingly, two compounds displayed up to 10-fold improved antileukemic activity with respect to SAHA; however, these compounds displayed antiproliferative activity similar to SAHA when assayed against solid tumor-derived cell lines. A 10-fold improvement in the leukemic vs peripheral blood mononuclear cell therapeutic ratio, with no evident in vivo toxicity toward blood cells, was also observed. The herein-described compounds and method of synthesis will provide invaluable tools to investigate the molecular mechanism responsible for the reported selectively improved antileukemic activity.
• COMPOUNDS AND METHODS FOR IMPROVING IMPAIRED ENDOGENOUS FIBRINOLYSIS USING HISTONE DEACETYLASE INHIBITORS
  申请人：Larsson Pia

  公开号：US20140051716A1

  公开（公告）日：2014-02-20

  There is provided a compound which is a histone deacetylase (HDAC) inhibitor, or a pharmaceutically acceptable ester, amide, solvate or salt thereof, for use in: (I) treating or preventing a pathological condition associated with excess fibrin deposition and/or thrombus formation; and/or (II) potentiating the degradation of fibrin deposits and preventing such deposits associated with pathological conditions or which may lead to such conditions, wherein the HDAC inhibitor, and the dose thereof, is as described in the description. There is also provided valproic acid, or a pharmaceutically acceptable salt thereof, for use in improving or normalizing endogenous fibrinolysis impaired by local or systemic inflammation.
• Racemization free longer N-terminal peptide hydroxamate synthesis on solid support using ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate
  作者：Srinivasa Rao Manne、Kishore Thalluri、Rajat Subhra Giri、Ashim Paul、Bhubaneswar Mandal

  DOI：10.1016/j.tetlet.2015.09.084

  日期：2015.10

  protocol for the synthesis of peptide hydroxamic acids directly from carboxylic/amino acids by ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate in the presence of DIPEA/DMAP at room temperature is described. The compatibility of this method with Fmoc based solid phase peptide synthesis (SPPS) is also demonstrated by synthesizing three relatively large N-terminal peptide hydroxamic acids on resin. Also

  在室温下，在DIPEA / DMAP存在下，由2-（叔丁氧基羰基氧基亚氨基）-2-氰基乙酸乙酯直接从羧酸/氨基酸直接合成肽异羟肟酸的简便，高效，无消旋，环境友好的方案是描述。该方法与基于Fmoc的固相肽合成（SPPS）的兼容性还通过在树脂上合成三种相对较大的N端肽异羟肟酸来证明。同样，一些生物学上重要的异羟肟酸酯是使用该方案合成的。