2'-monomehtyl-2-ethyl-1'-oxa-DCP | 1337971-49-9

• 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'-monomehtyl-2-ethyl-1'-oxa-DCP
• 英文别名: [(8S,9S,10R)-2-ethyl-8-methyl-4-oxo-10-[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy-9,10-dihydro-8H-pyrano[2,3-f]chromen-9-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 1337971-49-9
• 化学式: C₃₅H₄₀O₁₁
• 分子量: 636.696
• InChiKey: UPJMRSIIYYLXAY-CYFHKMNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  46
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-ethyl-7-hydroxy-4H-chromen-4-one 在 4-二甲氨基吡啶 、 potassium osmate(VI) dihydrate 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 N,N-二乙基苯胺 、 potassium iodide 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 、 2'-monomehtyl-2-ethyl-1'-oxa-DCP
  参考文献：
  名称：

  Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity

  摘要：

  Six 3'R,4'R-di-O-(S)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f] chromone (DCP) and two 3'R,4'R-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were designed, synthesized, and evaluated for inhibition of HIV-1(NL4-3) replication in TZM-bl cells. 2-Ethyl-2'-monomethyl-1'-oxa- and -1'-thia-DCP (5a, 6a), as well as 2-ethyl-1'-thia-DCP (7a) exhibited potent anti-HIV activity with EC(50) values of 30, 38 and 54 nM and therapeutic indexes of 152.6, 48.0 and 100.0, respectively, which were better than or comparable to those of the lead compound 2-ethyl-DCP in the same assay. 4-Methyl-1'-thia-DCK (8a) also showed significant inhibitory activity with an EC(50) of 128 nM and TI of 237.9. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.105

文献信息

• Solid-phase synthesis and pharmacological evaluation of novel nucleoside-tethered dinuclear platinum(II) complexes
  作者：Stefano D’Errico、Giorgia Oliviero、Vincenzo Piccialli、Jussara Amato、Nicola Borbone、Valentina D’Atri、Francesca D’Alessio、Rosa Di Noto、Francesco Ruffo、Francesco Salvatore、Gennaro Piccialli

  DOI：10.1016/j.bmcl.2011.07.104

  日期：2011.10

  Three novel inosine-based dinuclear platinum complexes have been synthesized via a solid-phase strategy. In these compounds, the metal is linked both to the N-7 of the purine nucleus and to the terminal amine group of a hexylamine side chain installed on N-1. Cis- or trans- diamine as well as ethylenediamine ligands are coordinated to platinum along with a chloride. The synthesised complexes were tested against four different human tumor cell lines. One of these complexes proved to be more cytotoxic than cisplatin against the MCF7 cancer cell line in a short-term exposure assay. (C) 2011 Elsevier Ltd. All rights reserved.
• Anti-AIDS agents 87. New bio-isosteric dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-khellactone (DCK) analogues with potent anti-HIV activity
  作者：Hong-Shan Liu、Shi-Qing Xu、Ming Cheng、Ying Chen、Peng Xia、Keduo Qian、Yi Xia、Zheng-Yu Yang、Chin-Ho Chen、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2011.07.105

  日期：2011.10

  Six 3'R,4'R-di-O-(S)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f] chromone (DCP) and two 3'R,4'R-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were designed, synthesized, and evaluated for inhibition of HIV-1(NL4-3) replication in TZM-bl cells. 2-Ethyl-2'-monomethyl-1'-oxa- and -1'-thia-DCP (5a, 6a), as well as 2-ethyl-1'-thia-DCP (7a) exhibited potent anti-HIV activity with EC(50) values of 30, 38 and 54 nM and therapeutic indexes of 152.6, 48.0 and 100.0, respectively, which were better than or comparable to those of the lead compound 2-ethyl-DCP in the same assay. 4-Methyl-1'-thia-DCK (8a) also showed significant inhibitory activity with an EC(50) of 128 nM and TI of 237.9. (C) 2011 Elsevier Ltd. All rights reserved.