4-isopropyl-benzaldehyde semicarbazone | 950-07-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-isopropyl-benzaldehyde semicarbazone
• 英文别名: Cuminaldehyd-semicarbazon；p-Isopropylbenz-aldehyde semicarbazone；[(4-propan-2-ylphenyl)methylideneamino]urea
• CAS: 950-07-2
• 化学式: C₁₁H₁₅N₃O
• mdl: MFCD00448950
• 分子量: 205.26
• InChiKey: GUYURJHCOAZNNL-UHFFFAOYSA-N

物化性质

• 熔点：
  211 °C
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-isopropyl-benzaldehyde semicarbazone 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 生成 5-(4-异丙基苯基)-1,3,4-恶二唑-2-胺
  参考文献：
  名称：

  Synthesis and <i>in Vitro</i> Antitumor Activity of 1,3,4-Oxadiazole Derivatives Based on Benzisoselenazolone

  摘要：

  一系列基于苯并亚硒氮烯的 novel 1,3,4-噁二唑衍生物已被合成，并在体外测试了其对人癌细胞系的抗增殖活性：SSMC-7721（人肝癌细胞）、MCF-7（人乳腺癌细胞）和 A549（人肺癌细胞）。所有合成的化合物均表现出抗增殖活性，并对不同癌细胞表现出选择性细胞毒性。化合物 7d 和 7i 对 MCF-7 细胞表现出显著的抗增殖活性，其 IC50 值分别为 1.07 和 1.76 µM。化合物 7d 被发现是对 SSMC-7721 细胞最有效的化合物，其 IC50 值为 4.46 µM。

  DOI：

  10.1248/cpb.c12-00250
• 作为产物：
  描述：

  4-异丙基苯甲醛 生成 4-isopropyl-benzaldehyde semicarbazone
  参考文献：
  名称：

  27.β-芹菜烯

  摘要：

  DOI：

  10.1039/jr9380000119

文献信息

• A short synthesis of the parp inhibitor 2-(4-trifluoro-methylphenyl)benzimidazole-4-carboxamide (NU1077)
  作者：Steven C. Austen、John M. Kane

  DOI：10.1002/jhet.5570380427

  日期：2001.7

  A four-step synthesis of the PARP inhibitor 2-(4-trifluoromethylphenyl)benzimidazole-4-carboxamide (1, NU1077) is presented. Condensation of 2,3-diaminotoluene and 4-trifluoromethylbenzaldehyde afforded 4-methyl-2-(4-trifluoromethylphenyl)benzimidazole. Oxidation of the methyl group with potassium permanganate in warm t-butanol afforded the carboxylic acid that was converted to the corresponding carboxamide

  提出了一种四步合成PARP抑制剂2-（4-三氟甲基苯基）苯并咪唑-4-羧酰胺（1，NU1077）。2，3-二氨基甲苯和4-三氟甲基苯甲醛的缩合得到4-甲基-2-（4-三氟甲基苯基）苯并咪唑。在温暖的叔丁醇中用高锰酸钾氧化甲基，得到羧酸，其通过酰氯转化为相应的羧酰胺。
• Vogelesang, Recueil des Travaux Chimiques des Pays-Bas, 1943, vol. 62, p. 5,11
  作者：Vogelesang

  DOI：——

  日期：——
• Gehlen,H.; Moeckel,K., Justus Liebigs Annalen der Chemie, 1962, vol. 651, p. 133 - 136
  作者：Gehlen,H.、Moeckel,K.

  DOI：——

  日期：——
• Structural modification of cuminaldehyde thiosemicarbazone increases inhibition specificity toward aflatoxin biosynthesis and sclerotia development in Aspergillus flavus
  作者：Francesca Degola、Franco Bisceglie、Marianna Pioli、Sabrina Palmano、Lisa Elviri、Giorgio Pelosi、Tiziana Lodi、Francesco Maria Restivo

  DOI：10.1007/s00253-017-8426-y

  日期：2017.9

  Aspergillus flavus is an opportunistic mold that represents a serious threat for human and animal health due to its ability to synthesize and release, on food and feed commodities, different toxic secondary metabolites. Among them, aflatoxin B1 is one of the most dangerous since it is provided with a strong cancerogenic and mutagenic activity. Controlling fungal contamination on the different crops that may host A. flavus is considered a priority by sanitary authorities of an increasing number of countries due also to the fact that, owing to global temperature increase, the geographic areas that are expected to be prone to experience sudden A. flavus outbreaks are widening. Among the different pre- and post-harvest strategies that may be put forward in order to prevent fungal and/or mycotoxin contamination, fungicides are still considered a prominent weapon. We have here analyzed different structural modifications of a natural-derived compound (cuminaldehyde thiosemicarbazone) for their fungistatic and anti-aflatoxigenic activity. In particular, we have focused our attention on one of the compound that presented a prominent anti-aflatoxin specificity, and performed a set of physiological and molecular analyses, taking also advantage of yeast (Saccharomyces cerevisiae) cell as an experimental model.
• Joshi, Shrinivas D.; Dixit, Sheshagiri R.; More, Uttam A., Indian Journal of Heterocyclic Chemistry, 2014, vol. 24, # 2, p. 137 - 140
  作者：Joshi, Shrinivas D.、Dixit, Sheshagiri R.、More, Uttam A.、Kulkarni, Venkatrao H.

  DOI：——

  日期：——