2-mercapto-N-[6-(3-phenylureido)hexyl]acetamide | 827036-63-5

• 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: 2-mercapto-N-[6-(3-phenylureido)hexyl]acetamide
• 英文别名: BC-4-3；N-{6-[(Phenylcarbamoyl)amino]hexyl}-2-sulfanylacetamide；N-[6-(phenylcarbamoylamino)hexyl]-2-sulfanylacetamide
• CAS: 827036-63-5
• 化学式: C₁₅H₂₃N₃O₂S
• 分子量: 309.433
• InChiKey: ZOONFWOWCXQYQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.2
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercapto-N-[6-(3-phenylureido)hexyl]acetamide 在 氧气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到N-[6-(3-phenyl-ureido)-hexyl]-2-{[6-(3-phenyl-ureido)-hexylcarbamoyl]-methyldisulfanyl}-acetamide
  参考文献：
  名称：

  Histone deacetylase inhibitors and methods of use thereof

  摘要：

  这项发明提供了新型类别的HDAC抑制剂。还提供了一种使癌细胞对放疗的细胞毒作用敏感的方法，以及治疗癌症和治疗神经疾病的方法。此外，该发明还提供了包括该发明的HDAC抑制剂的药物组合物，以及包含一种HDAC抑制剂的容器的试剂盒。

  公开号：

  US20050014839A1
• 作为产物：
  描述：

  N-(6-aminohexyl)-2-tritylsulfanyl acetamide 在 三乙基硅烷 、 三氟乙酸 作用下， 生成 2-mercapto-N-[6-(3-phenylureido)hexyl]acetamide
  参考文献：
  名称：

  Chemistry and biology of mercaptoacetamides as novel histone deacetylase inhibitors

  摘要：

  A series of mercaptoacetamides were designed and synthesized as novel histone deacetylase inhibitors with the aid of modeling. Their ability to inhibit HDAC activity and their effects on cancer cell growth were investigated. Some compounds exhibit better HDAC inhibitory activity than SAHA. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.006

文献信息

• Concise Syntheses and Antitumor Activities of a-Hydroxy(mercapto)amide Derivatives
  作者：Y.X. Li、Z. Qiu

  DOI：10.14233/ajchem.2014.15894

  日期：——

  A novel process for preparing a-hydroxy(mercapto)-N-[6-(3-phenylureido)hexyl]amide derivatives was described and three new compounds 8-10 were synthesized. The antitumor activities on Hut102, MCF7 and HepG2 of the compounds 7-10 were assayed. The results showed that the target compounds 7-10 exhibited some antitumor activities against tumor cell lines.

  介绍了一种制备 a-羟基（巯基）-N-[6-(3-苯基脲基)己基]酰胺衍生物的新工艺，并合成了三种新化合物 8-10。对 7-10 号化合物在 Hut102、MCF7 和 HepG2 上的抗肿瘤活性进行了测定。结果表明，目标化合物 7-10 对肿瘤细胞株具有一定的抗肿瘤活性。
• Histone Deacetylase Inhibitors and Methods of Use Thereof
  申请人：Kozikowski Alan P.

  公开号：US20110098504A1

  公开（公告）日：2011-04-28

  The invention provides novel classes of HDAC inhibitors. Methods of sensitizing a cancer cell to the cytotoxic effects of radiotherapy are also provided as well as methods for treating cancer and methods for treating neurological diseases. Additionally, the invention further provides pharmaceutical compositions comprising an HDAC inhibitor of the invention, and kits comprising a container containing an HDAC inhibitor of the invention.

  本发明提供了新型的HDAC抑制剂类。同时提供了一种使癌细胞对放疗的细胞毒性效应敏感的方法，以及治疗癌症和神经疾病的方法。此外，本发明还提供了包含本发明中的HDAC抑制剂的制药组合物，以及包含一个含有本发明中的HDAC抑制剂的容器的套装。
• Functional Differences in Epigenetic ModulatorsSuperiority of Mercaptoacetamide-Based Histone Deacetylase Inhibitors Relative to Hydroxamates in Cortical Neuron Neuroprotection Studies
  作者：Alan P. Kozikowski、Yufeng Chen、Arsen Gaysin、Bin Chen、Melissa A. D'Annibale、Carla M. Suto、Brett C. Langley

  DOI：10.1021/jm070178x

  日期：2007.6.1

  We compare the ability of two structurally different classes of epigenetic modulators, namely, histone deacetylase (HDAC) inhibitors containing either a hydroxamate or a mercaptoacetamide as the zinc binding group, to protect cortical neurons in culture from oxidative stress-induced death. This study reveals that some of the mercaptoacetamide-based HDAC inhibitors are fully protective, whereas the hydroxamates show toxicity at higher concentrations. Our present results appear to be consistent with the possibility that the mercaptoacetamide-based HDAC inhibitors interact with a different subset of the HDAC isozymes [less activity at HDAC1 and 2 correlates with less inhibitor toxicity], or alternatively, are interacting selectively with only the cytoplasmic HDACs that are crucial for protection from oxidative stress.
• A Series of Potent and Selective, Triazolylphenyl-Based Histone Deacetylases Inhibitors with Activity against Pancreatic Cancer Cells and <i>Plasmodium falciparum</i>
  作者：Yufeng Chen、Miriam Lopez-Sanchez、Doris N. Savoy、Daniel D. Billadeau、Geoffrey S. Dow、Alan P. Kozikowski

  DOI：10.1021/jm701606b

  日期：2008.6.1

  The discovery of the rules governing the inhibition of the various HDAC isoforms is likely to be key to identifying improved therapeutics that act as epigenetic modulators of gene transcription. Herein we present results on the modification of the CAP region of a set of triazolylphenyl-based HDACIs, and show that the nature of substitution on the phenyl ring plays a role in their selectivity for HDAC1 versus HDAC6, with low to moderate selectivity (2-51-fold) being achieved. In light of the valuable selectivity and potency that were identified for the triazolylphenyl ligand 6b in the inhibition of HDAC6 (IC50 = 1.9 nM), this compound represents a valuable research tool and a candidate for further chemical modifications. Lastly, these new HDACIs were studied for both their anticancer and antimalarial activity, which serve to validate the superior activity of the HDACI 10c.
• HISTONE DEACETYLASE INHIBITORS AND METHODS OF USE THEREOF
  申请人：GEORGETOWN UNIVERSITY

  公开号：EP1644323A2

  公开（公告）日：2006-04-12