N,N'-dimethyl-N,N'-hexamethylenebis(acetamide) | 105859-85-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-dimethyl-N,N'-hexamethylenebis(acetamide)
• 英文别名: N,N'-Dimethyl-HMBA；N-[6-[acetyl(methyl)amino]hexyl]-N-methylacetamide
• CAS: 105859-85-6
• 化学式: C₁₂H₂₄N₂O₂
• 分子量: 228.335
• InChiKey: SGHJEJIGUKIFTN-UHFFFAOYSA-N

物化性质

• 沸点：
  138 °C(Press: 0.1 Torr)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基乙酰胺 、 1,6-二溴己烷 以 四氢呋喃 、 水 为溶剂， 以53%的产率得到N,N'-dimethyl-N,N'-hexamethylenebis(acetamide)
  参考文献：
  名称：

  Chemical differentiating agents

  摘要：

  已找到几种己二酰胺的类似物，它们被发现是有效的分化剂。其中最有效的化合物是3,3'-(1,6-己二基)双[5,5-二甲基-2,4-咪唑啉二酮]。

  公开号：

  US04882346A1

文献信息

• [EN] COMPOSITIONS AND METHODS FOR MODULATING HEXIM1 EXPRESSION<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE MODULATION DE L'EXPRESSION D'HEXIM1
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2015116968A1

  公开（公告）日：2015-08-06

  The potency of a series of Hexamethylene bis-acetamide (HMBA) derivatives of formula I, that induce Hexamethylene bis-acetamide inducible protein 1 (HEXIM1 ) was determined in cancer cells. The method of inducing HEXIM1 expression and cell differentiation in cancer and HIV cells are disclosed. Optimization of HMBA analogs that are symmetrical and unsymmetrical are also discussed.

  一系列诱导己六亚甲基双乙酰胺（HMBA）衍生物（化学式I）的效力，能够诱导己六亚甲基双乙酰胺诱导蛋白1（HEXIM1）在癌细胞中的表达已经确定。揭示了在癌细胞和HIV细胞中诱导HEXIM1表达和细胞分化的方法。还讨论了对称和非对称的HMBA类似物的优化。
• Chemical differentiating agents. Differentiation of HL-60 cells by hexamethylenebis[acetamide]analogs
  作者：Alberto Haces、Theodore R. Breitman、John S. Driscoll

  DOI：10.1021/jm00385a025

  日期：1987.2

  Hexamethylenebis[acetamide] (HMBA) is an agent in clinical trial that induces differentiation of certain types of tumor cells to nonmalignant phenotypes. In an attempt to discover a more potent compound, a number of bis-functionalized amides, imides, and hydrazine derivatives of HMBA were prepared and evaluated in vitro with the HL-60 human promyelocytic leukemia cell line. Among the compounds evaluated, the 5,5-dimethylhydantoin derivative is almost 10 times more potent than HMBA in inducing differentiation. The bis-imide, diacetyl-HMBA, is both more potent and effective than its parent compound. Six of the 16 compounds evaluated cause at least 20% differentiation. An inverse relationship between the degree of differentiation and the percentage of viable cells is described for HMBA and its analogues.
• Lead optimization of HMBA to develop potent HEXIM1 inducers
  作者：Bo Zhong、Rati Lama、Wannarasmi Ketchart、Monica M. Montano、Bin Su

  DOI：10.1016/j.bmcl.2014.01.025

  日期：2014.3

  The potency of a series of Hexamethylene bis-acetamide (HMBA) derivatives inducing Hexamethylene bis-acetamide inducible protein 1 (HEXIM1) was determined in LNCaP prostate cancer cells. Several compounds with unsymmetrical structures showed significantly improved activity. Distinct from HMBA, these analogs have increased hydrophobicity and can improve the short half-life of HMBA, which is one of the factors that have limited the application of HMBA in clinics. The unsymmetrical scaffolds of the new analogs provide the basis for further lead optimization of the compounds using combinatorial chemistry strategy. Published by Elsevier Ltd.
• DRISEOLL, JOHN S.;HACES, ALBERTE;BREITMAN, THEODORE
  作者：DRISEOLL, JOHN S.、HACES, ALBERTE、BREITMAN, THEODORE

  DOI：——

  日期：——
• HACES A.; BREITMAN T. R.; DRISCOLL J. S., J. MED. CHEM., 30,(1987) N 2, 405-409
  作者：HACES A.、 BREITMAN T. R.、 DRISCOLL J. S.

  DOI：——

  日期：——