(E)-4-(tert-butyl)-N'-(4-hydroxybenzylidene)benzohydrazide | 1351366-64-7

• 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: (E)-4-(tert-butyl)-N'-(4-hydroxybenzylidene)benzohydrazide
• 英文别名: (E)-4-(tert-butyl)-N’-(4-hydroxybenzylidene)benzohydride；4-tert-butyl-N'-[(E)-(4-hydroxyphenyl)methylidene]benzohydrazide；4-tert-butyl-N-[(E)-(4-hydroxyphenyl)methylideneamino]benzamide
• CAS: 1351366-64-7
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: GTWSTDDXEJZVLS-XDHOZWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对叔丁基苯甲酰肼 、 对羟基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以34%的产率得到(E)-4-(tert-butyl)-N'-(4-hydroxybenzylidene)benzohydrazide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of N-oxide derivatives with potent in vivo antileishmanial activity

  摘要：

  利什曼病是一种影响主要发展中国家居民的1200万人的被忽视的疾病。在这项研究中，合成了24种新的含氧化物的化合物，随后评估了它们的抗利什曼病活性。其中，一种呋喃氧化物衍生物4f在这方面表现尤为出色，对婴儿利什曼体形式的EC50值为3.6μM，对小鼠腹膜巨噬细胞的CC50值超过500μM。体外研究表明，4f可能通过双重作用发挥作用，经生物转化后释放一氧化氮，并抑制半胱氨酸蛋白酶CPB（IC50：4.5μM）。使用急性感染模型的体内研究表明，7.7毫克/千克的4f化合物可使感染婴儿利什曼体的BALB/c小鼠肝脏和脾脏中的寄生虫负担减少约90%。总的来说，这些结果突出了呋喃氧化物4f作为一种有前途的化合物，值得进一步评估其作为抗利什曼病药物的潜力。

  DOI：

  10.1371/journal.pone.0259008

文献信息

• Synthesis, antioxidant and photoprotection activities of hybrid derivatives useful to prevent skin cancer
  作者：Juliana Santana Reis、Marcos Antonio Corrêa、Man Chin Chung、Jean Leandro dos Santos

  DOI：10.1016/j.bmc.2014.03.017

  日期：2014.5

  Chronic ultraviolet (UV) radiation exposure is a major cause of skin cancer. A novel series of hybrid derivatives (I-VIII) for use in sunscreen formulations were synthesized by molecular hybridization of t-resveratrol, avobenzone, and octyl methoxycinnamate, and were characterized. The antioxidant activity values for VIII were comparable than to those of t-resveratrol. Compounds I-III and VI demonstrated Sun Protector Factor superior to that of t-resveratrol. Compounds I and IV-VIII were identified as new, broad-spectrum UVA filters while II-III were UVB filters. In conclusion, novel hybrid derivatives with antioxidant effects have emerged as novel photoprotective agents for the prevention of skin cancer. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of N-oxide derivatives with potent in vivo antileishmanial activity
  作者：Leandro da Costa Clementino、Guilherme Felipe Santos Fernandes、Igor Muccilo Prokopczyk、Wilquer Castro Laurindo、Danyelle Toyama、Bruno Pereira Motta、Amanda Martins Baviera、Flávio Henrique-Silva、Jean Leandro dos Santos、Marcia A. S. Graminha

  DOI：10.1371/journal.pone.0259008

  日期：——

  Leishmaniasis is a neglected disease that affects 12 million people living mainly in developing countries. Herein, 24 new N-oxide-containing compounds were synthesized followed by in vitro and in vivo evaluation of their antileishmanial activity. Compound 4f, a furoxan derivative, was particularly remarkable in this regard, with EC₅₀ value of 3.6 μM against L. infantum amastigote forms and CC₅₀ value superior to 500 μM against murine peritoneal macrophages. In vitro studies suggested that 4f may act by a dual effect, by releasing nitric oxide after biotransformation and by inhibiting cysteine protease CPB (IC₅₀: 4.5 μM). In vivo studies using an acute model of infection showed that compound 4f at 7.7 mg/Kg reduced ~90% of parasite burden in the liver and spleen of L. infantum-infected BALB/c mice. Altogether, these outcomes highlight furoxan 4f as a promising compound for further evaluation as an antileishmanial agent.

  利什曼病是一种影响主要发展中国家居民的1200万人的被忽视的疾病。在这项研究中，合成了24种新的含氧化物的化合物，随后评估了它们的抗利什曼病活性。其中，一种呋喃氧化物衍生物4f在这方面表现尤为出色，对婴儿利什曼体形式的EC50值为3.6μM，对小鼠腹膜巨噬细胞的CC50值超过500μM。体外研究表明，4f可能通过双重作用发挥作用，经生物转化后释放一氧化氮，并抑制半胱氨酸蛋白酶CPB（IC50：4.5μM）。使用急性感染模型的体内研究表明，7.7毫克/千克的4f化合物可使感染婴儿利什曼体的BALB/c小鼠肝脏和脾脏中的寄生虫负担减少约90%。总的来说，这些结果突出了呋喃氧化物4f作为一种有前途的化合物，值得进一步评估其作为抗利什曼病药物的潜力。