methyl N-(anthracen-9-ylmethylideneamino)carbamodithioate | 1237537-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: methyl N-(anthracen-9-ylmethylideneamino)carbamodithioate
• CAS: 1237537-65-3
• 化学式: C₁₇H₁₄N₂S₂
• 分子量: 310.444
• InChiKey: FTRKNQSKBHNQQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl N-(anthracen-9-ylmethylideneamino)carbamodithioate 在 羟胺 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.96h， 生成 1-(anthracen-9-ylmethylideneamino)-3-hydroxy-2-propan-2-ylguanidine
  参考文献：
  名称：

  Effect of substitution at N″-position of N′-hydroxy-N-amino guanidines on tumor cell growth

  摘要：

  Structural modification of one of our earlier reported lead molecule (ABNM13) has been carried out to study the effect of different substituents at the N ''-position of N-hydroxy-N'-amino guanidines (HAGs) on their anticancer activity. Compounds with electron donating substituents were found to be less active. In contrast, those with electron withdrawing groups were found favorable for anticancer activity. The obtained results provide significant SAR information that may be useful for further drug designing with HAGs. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.048
• 作为产物：
  描述：

  肼基二硫代甲酸甲酯 、 9-蒽甲醛 以 甲醇 为溶剂， 以61%的产率得到methyl N-(anthracen-9-ylmethylideneamino)carbamodithioate
  参考文献：
  名称：

  Methyl-2-arylidene hydrazinecarbodithioates: synthesis and biological activity

  摘要：

  摘要：甲基-2-芳基亚硫酰肼-卡巴二硫酸酯尽管其金属配合物因其生物活性而被广泛报道，但并未引起研究人员的特别关注。本研究考察了十二种甲基-2-芳基亚硫酰肼-卡巴二硫酸酯的细胞静止和抗病毒活性，这些化合物被许多研究人员报告为噻唑半脒的合成中间体和其金属配合物的制备。具有三齿配体特征的IIc、IIi和IIl化合物被发现对HL60人类前粒细胞白血病细胞具有最低的IC50值（分别为6.5μM、≈1μM和0.8μM）。它们对人类胚胎肺（HEL）成纤维细胞增殖抑制最强（分别为5.3μM、17μM和2.6μM）。化合物IIc和IIl对野生型单纯疱疹病毒（HSV）、带状疱疹病毒（VZV）和阿昔洛韦耐药HSV具有抗病毒活性；然而，这些活性在化合物显著抑制HL60和HEL细胞增殖的浓度下被观察到。

  DOI：

  10.2478/s11696-013-0346-4

文献信息

• Design, synthesis and anticancer activity of piperazine hydroxamates and their histone deacetylase (HDAC) inhibitory activity
  作者：Bhadaliya Chetan、Mahesh Bunha、Monika Jagrat、Barij Nayan Sinha、Philipp Saiko、Geraldine Graser、Thomas Szekeres、Ganapathy Raman、Praveen Rajendran、Dhatchana Moorthy、Arijit Basu、Venkatesan Jayaprakash

  DOI：10.1016/j.bmcl.2010.05.020

  日期：2010.7

  Six compounds were synthesized with piperazine in linker region and hydroxamate as Zinc Binding Group ( ZBG). They were screened against three cancer cell-lines (NCIH460; HCT116; U251). Compounds 5c and 5f with GI(50) value of 9.33 +/- 1.3 mu M and 12.03 +/- 4 mu M, respectively, were tested for their inhibitory potential on hHDAC8. Compound 5c had IC(50) of 33.67 mu M. Compounds were also screened for their anticancer activity against HL60 human promyelocytic leukemia cell line due to the presence of pharmacophoric features of RR inhibitors in them. Compound 5c had IC(50) of 0.6 mu M at 48 h. (c) 2010 Elsevier Ltd. All rights reserved.