naphthalene-1-carbaldehyde 4-m-tolyl-thiosemicarbazone | 7701-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-1-carbaldehyde 4-m-tolyl-thiosemicarbazone
• 英文别名: Naphthyl-1-carbaldehyd-<4-m-tolyl-thiosemicarbazon>；1-(3-Methylphenyl)-3-(naphthalen-1-ylmethylideneamino)thiourea；1-(3-methylphenyl)-3-(naphthalen-1-ylmethylideneamino)thiourea
• CAS: 7701-06-6
• 化学式: C₁₉H₁₇N₃S
• 分子量: 319.43
• InChiKey: XTCQDDNKKYMDIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  naphthalene-1-carbaldehyde 4-m-tolyl-thiosemicarbazone 、 2-氯丙酸 生成 naphthalene-1-carbaldehyde (5-methyl-4-oxo-3-m-tolyl-thiazolidin-2-ylidene)-hydrazone
  参考文献：
  名称：

  Trivedi,J.P.; Shah,I.D., Journal of the Indian Chemical Society, 1966, vol. 43, p. 275 - 276

  摘要：

  DOI：
• 作为产物：
  描述：

  1-萘甲醛 、 3-甲基苯基氨基硫脲 以 乙醇 、 水 为溶剂， 反应 0.83h， 生成 naphthalene-1-carbaldehyde 4-m-tolyl-thiosemicarbazone
  参考文献：
  名称：

  Structure–activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

  摘要：

  2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC50 = 1.1 mu M) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of alpha-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.035

文献信息

• Structure–activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition
  作者：Pillaiyar Thanigaimalai、Eeda Venkateswara Rao、Ki-Cheul Lee、Vinay K. Sharma、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2011.12.035

  日期：2012.1

  2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC50 = 1.1 mu M) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of alpha-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Trivedi,J.P.; Shah,I.D., Journal of the Indian Chemical Society, 1966, vol. 43, p. 275 - 276
  作者：Trivedi,J.P.、Shah,I.D.

  DOI：——

  日期：——