2,3,8,8-tetramethyl-N-(naphthalen-1-yl)-4-oxo-2,3,4,8-tetrahydropyrano[2,3-f]chromene-6-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,3,8,8-tetramethyl-N-(naphthalen-1-yl)-4-oxo-2,3,4,8-tetrahydropyrano[2,3-f]chromene-6-carboxamide
• 英文别名: 2,3,8,8-tetramethyl-N-naphthalen-1-yl-4-oxo-2,3-dihydropyrano[2,3-h]chromene-6-carboxamide
• 化学式: C₂₇H₂₅NO₄
• 分子量: 427.5
• InChiKey: JMIXLMDGJOEDLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,8,8-tetramethyl-4-oxo-2,3,4,8-tetrahydropyrano[2,3-f]chromene-6-carboxylic acid 、 1-萘胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.08h， 以70%的产率得到2,3,8,8-tetramethyl-N-(naphthalen-1-yl)-4-oxo-2,3,4,8-tetrahydropyrano[2,3-f]chromene-6-carboxamide
  参考文献：
  名称：

  Natural product-inspired rational design, synthesis and biological evaluation of 2,3-dihydropyrano[2,3- f ]chromen-4(8 H )-one based hybrids as potential mitochondrial apoptosis inducers

  摘要：

  Synthesis of novel pyranochromanone amide hybrids, by combining pyranochromanone pharmacophore and privileged scaffolds such as 2-amino-1,3,4-thiadiaole/2-aminothiazole/aminopyridine/amino-naphthalene and anti-cancer evaluation of a series led us to discover a series of new chemical entities (NCEs) showing broad spectrum of anti-cancer activity against three different human cancer cell lines (MCF-7, A549 and HeLa), at IC50 values ranging from 14.3 to 97.8 mu M. Among them, some compounds such as 15b,15d, 20a and 20b displayed excellent activity against breast cancer cell line MCF-7. Detailed biological studies such as AO/EB dual staining, Hoechst 33342 staining, FACS analysis of mitochondrial membrane potential (Delta psi(m)) using JC-1 dye and DNA fragmentation confirmed the apoptosis induced by the hybrids. Gene expression studies by Real time RT-PCR has shown that these compounds are efficient regulator of anti-apoptotic gene Bcl-2. Western blot analysis also revealed that these compounds persuade apoptosis through intrinsic pathway by up-regulating the pro-apoptotic protein Bax and down regulating the anti-apoptotic protein Bcl-2. Molecular docking studies reveal that compounds 15b and 20b binds efficiently with BcI-2 promoter G-quadruplex. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.06.044

文献信息

• Natural product-inspired rational design, synthesis and biological evaluation of 2,3-dihydropyrano[2,3- f ]chromen-4(8 H )-one based hybrids as potential mitochondrial apoptosis inducers
  作者：Palaniappan Sakthivel、Andivelu Ilangovan、Mahabir Prasad Kaushik

  DOI：10.1016/j.ejmech.2016.06.044

  日期：2016.10

  Synthesis of novel pyranochromanone amide hybrids, by combining pyranochromanone pharmacophore and privileged scaffolds such as 2-amino-1,3,4-thiadiaole/2-aminothiazole/aminopyridine/amino-naphthalene and anti-cancer evaluation of a series led us to discover a series of new chemical entities (NCEs) showing broad spectrum of anti-cancer activity against three different human cancer cell lines (MCF-7, A549 and HeLa), at IC50 values ranging from 14.3 to 97.8 mu M. Among them, some compounds such as 15b,15d, 20a and 20b displayed excellent activity against breast cancer cell line MCF-7. Detailed biological studies such as AO/EB dual staining, Hoechst 33342 staining, FACS analysis of mitochondrial membrane potential (Delta psi(m)) using JC-1 dye and DNA fragmentation confirmed the apoptosis induced by the hybrids. Gene expression studies by Real time RT-PCR has shown that these compounds are efficient regulator of anti-apoptotic gene Bcl-2. Western blot analysis also revealed that these compounds persuade apoptosis through intrinsic pathway by up-regulating the pro-apoptotic protein Bax and down regulating the anti-apoptotic protein Bcl-2. Molecular docking studies reveal that compounds 15b and 20b binds efficiently with BcI-2 promoter G-quadruplex. (C) 2016 Elsevier Masson SAS. All rights reserved.