1-[(benzylamino)methylidene]-7-[8-[(benzylamino)methylidene]-1,6-dihydroxy-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-4-propan-2-ylnaphthalen-2-one

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1-[(benzylamino)methylidene]-7-[8-[(benzylamino)methylidene]-1,6-dihydroxy-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-4-propan-2-ylnaphthalen-2-one
• 化学式: C₄₄H₄₄N₂O₆
• 分子量: 696.843
• InChiKey: HABYYKGPDAAKDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  52.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  139.12
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  gossypol acetic acid 、 苄胺 以 乙醇 为溶剂， 以93%的产率得到1-[(benzylamino)methylidene]-7-[8-[(benzylamino)methylidene]-1,6-dihydroxy-3-methyl-7-oxo-5-propan-2-ylnaphthalen-2-yl]-3,8-dihydroxy-6-methyl-4-propan-2-ylnaphthalen-2-one
  参考文献：
  名称：

  具有疏水性线性酯的棉酚具有增强的抗肿瘤活性，可作为抗凋亡蛋白的抑制剂。

  摘要：

  鉴定了一系列衍生自非天然线性氨基酸甲基酯的棉酚席夫碱，其抗癌活性比棉酚和ABT-199强得多。这是活性增加的棉酚席夫碱的第一个例子。对棉酚席夫碱侧链的研究表明，独特的抗癌作用是通过引入疏水性酯基实现的。优化的产品对NCI-60肿瘤细胞系表现出低的微摩尔泛抗肿瘤活性，这有望进一步开发药物。还使用抗凋亡蛋白（Bcl-2和Mcl-1）抑制FP测定法对其细胞活性的初步作用机理进行了研究。

  DOI：

  10.1021/acsmedchemlett.6b00302

文献信息

• Gossypol with Hydrophobic Linear Esters Exhibits Enhanced Antitumor Activity as an Inhibitor of Antiapoptotic Proteins
  作者：Yuzhi Lu、Shuangchan Wu、Yuan Yue、Si He、Jun Li、Jun Tang、Wei Wang、Hai-Bing Zhou

  DOI：10.1021/acsmedchemlett.6b00302

  日期：2016.12.8

  A series of gossypol Schiff bases that were derived from unnatural linear amino acid methyl esters were identified and found to be much more potent than gossypol and ABT-199 in terms of anticancer activity. This is the first example of gossypol Schiff bases with increased activity. The investigation of the Schiff base side chain of gossypol revealed that the unique anticancer effect was achieved by

  鉴定了一系列衍生自非天然线性氨基酸甲基酯的棉酚席夫碱，其抗癌活性比棉酚和ABT-199强得多。这是活性增加的棉酚席夫碱的第一个例子。对棉酚席夫碱侧链的研究表明，独特的抗癌作用是通过引入疏水性酯基实现的。优化的产品对NCI-60肿瘤细胞系表现出低的微摩尔泛抗肿瘤活性，这有望进一步开发药物。还使用抗凋亡蛋白（Bcl-2和Mcl-1）抑制FP测定法对其细胞活性的初步作用机理进行了研究。
• Synthesis and antiviral, insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine, oxime or hydrazine moiety
  作者：Ling Li、Zheng Li、Kailiang Wang、Yuxiu Liu、Yongqiang Li、Qingmin Wang

  DOI：10.1016/j.bmc.2015.08.015

  日期：2016.2

  Gossypol is a part of the cotton plant's defense system against pathogens and herbivorous insects. To discover gossypol analogs with broad spectrum and high activity, a series of gossypol alkylamine Schiff base, oxime and hydrazone derivatives were synthesised and bioassayed. The biological results indicated that most of these derivatives exhibited higher anti-TMV activity than gossypol. Interestingly, the activities of compounds 10, 15, 18, 20, 23 and 26 were much higher than that of ribavirin. Furthermore, compound 26, which was low toxicity to rat, showed better activity than control plant virus inhibitors in the field. Additionally, allyl amine Schiff base (9) displayed remarkable insecticidal activities against Mythimna separata, Helicoverpa armigera and Ostrinia nubilalis, whereas (pyridin-3-yl) methanamine Schiff base (13) showed excellent activity against Culex pipiens pallens. The fungicidal results revealed that all of compounds exhibited good activity against Physalospora piricola. (C) 2015 Elsevier Ltd. All rights reserved.