4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone | 29201-97-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone
• 英文别名: 5,6,7,8,3'-Pentamethoxy-4'-benzyloxyflavone；2-(4-benzyloxy-3-methoxy-phenyl)-5,6,7,8-tetramethoxy-chromen-4-one；5,6,7,8-Tetramethoxy-2-(3-methoxy-4-phenylmethoxyphenyl)chromen-4-one
• CAS: 29201-97-6
• 化学式: C₂₇H₂₆O₈
• 分子量: 478.499
• InChiKey: GOYYGHFRMDFYBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以88%的产率得到4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone
  参考文献：
  名称：

  Nobiletin代谢产物：合成和对基质金属蛋白酶9产生的抑制活性

  摘要：

  通过高度氧化的苯乙酮衍生物开发了nobiletin代谢产物的多样化合成。我们使用市售的3,4,5-三甲氧基苯甲酸甲酯作为起始原料，以简化关键中间体2'-羟基-3'，4'，5'，6'-四甲氧基苯乙酮（I）的制备。这些代谢物显示出对人晶状体上皮细胞中基质金属蛋白酶9产生的强抑制活性。

  DOI：

  10.1016/j.bmcl.2011.05.121
• 作为产物：
  描述：

  (1H-benzo[d][1,2,3]triazol-1-yl)(4-(benzyloxy)-3-methoxyphenyl)methanone 在 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4'-benzyloxy-3',5,6,7,8-pentamethoxyflavone
  参考文献：
  名称：

  Concise synthesis of polymethoxyflavone sudachitin and its derivatives, and biological evaluations

  摘要：

  We accomplished a divergent synthesis of sudachitin (2), a polymethoxyflavone isolated from citrus fruits, and six derivatives from acetophenone 9, which was an intermediate in our previous synthesis of nobiletin (1). Compound 2 enhanced glucose-induced insulin secretion in INS-1D cells, but was less potent than 1. Compared with 1, compound 2 and two derivatives were more potent inhibitors of cAMP-specific phosphodiesterase. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2018.03.064

文献信息

• Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives
  作者：Tomohiro Asakawa、Hiroto Sagara、Masaki Kanakogi、Aiki Hiza、Yuta Tsukaguchi、Takahiro Ogawa、Miho Nakayama、Hitoshi Ouchi、Makoto Inai、Toshiyuki Kan

  DOI：10.1021/acs.oprd.9b00091

  日期：2019.4.19

  We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response

  我们提出了适用于一百克规模的聚甲氧基化柑桔黄酮Nobiletin的实用合成方法。该化合物及其衍生物的现成可用性将有助于对其生物学活性的详细化学生物学研究，包括通过cAMP依赖性蛋白激酶A /细胞外信号相关蛋白激酶/ cAMP反应元件结合蛋白途径激活信号。
• COGNITIVE IMPAIRMENT AMELIORANT
  申请人：Yamaguchi Kikuji

  公开号：US20110287106A1

  公开（公告）日：2011-11-24

  A cognitive impairment ameliorant is provided that is useful for the prevention or treatment of cognitive impairment, and particularly Alzheimer's disease. The cognitive impairment ameliorant contains royal jelly as an active ingredient thereof.

  提供一种认知障碍改善剂，可用于预防或治疗认知障碍，特别是阿尔茨海默病。该认知障碍改善剂包含蜂王浆作为其活性成分。
• COGNITIVE DISORDER-AMELIORATING AGENT
  申请人：Japan Royal Jelly Co., Ltd.

  公开号：EP2311472B1

  公开（公告）日：2014-03-05
• Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines
  作者：Shiming Li、Min-Hsiung Pan、Ching-Shu Lai、Chih-Yu Lo、Slavik Dushenkov、Chi-Tang Ho

  DOI：10.1016/j.bmc.2007.03.021

  日期：2007.5

  Fifteen polymethoxyflavones (PMFs) and hydroxylated PMFs were isolated from sweet orange (Citrus sinensis) peel extract and synthesized to investigate their biological activity. All obtained compounds were tested in HL-60 cancer cell proliferation and apoptosis induction assays. While some PMFs and hydroxylated PMFs had moderate anti-carcinogenic activities, 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone and 5-hydroxy- 3,6,7,8,3',4'-hexamethoxyflavone showed strong inhibitory activities against the proliferation and induced apoptosis of HL-60 cell lines. (c) 2007 Elsevier Ltd. All rights reserved.
• B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production
  作者：Tetsuta Oshitari、Yuji Okuyama、Yoshiki Miyata、Hiroshi Kosano、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1016/j.bmc.2011.10.001

  日期：2011.12

  Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-alpha-stimulated human lens epithelial cells, the 2'-hydroxylated analogue 5a exerted marked inhibitory effects (IC50: 0.4 mu M) on PMA-treated cells, which were 170-fold more potent than those on TNF-alpha-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9. (C) 2011 Elsevier Ltd. All rights reserved.