6,3',4'-trihydroxyflavanone

• 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: 6,3',4'-trihydroxyflavanone
• 英文别名: 2-(3,4-dihydroxyphenyl)-6-hydroxychroman-4-one；naringenin；2-(3,4-Dihydroxy-phenyl)-6-hydroxy-chroman-4-on；2-(3,4-dihydroxyphenyl)-6-hydroxy-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: SHYJMIHVPPCBNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-hydroxy-3',4'-dimethoxyflavanone 在 吡啶盐酸盐 作用下， 反应 7.0h， 以93%的产率得到6,3',4'-trihydroxyflavanone
  参考文献：
  名称：

  A novel Synthesis of Naringenin and Related Flavanones

  摘要：

  报告了制备柚皮素（4′,5,7-三羟基黄烷酮）的高效方法，该方法易于推广。这些方法还适用于其他三种黄烷酮（6-羟基黄烷酮、6,4′-二羟基黄烷酮、6,3′,4′-三羟基黄烷酮）。

  DOI：

  10.3184/174751914x14145820775908

文献信息

• Comparing Drug Images and Repurposing Drugs with BioGPS and FLAPdock: The Thymidylate Synthase Case
  作者：Lydia Siragusa、Rosaria Luciani、Chiara Borsari、Stefania Ferrari、Maria Paola Costi、Gabriele Cruciani、Francesca Spyrakis

  DOI：10.1002/cmdc.201600121

  日期：2016.8.5

  Repurposing and repositioning drugs has become a frequently pursued and successful strategy in the current era, as new chemical entities are increasingly difficult to find and get approved. Herein we report an integrated BioGPS/FLAPdock pipeline for rapid and effective off-target identification and drug repurposing. Our method is based on the structural and chemical properties of protein binding sites

  随着新化学实体越来越难以找到和获得批准，重新定位和重新定位药物已成为当前时代的一种成功追求的成功策略。本文中，我们报告了一条集成的BioGPS / FLAPdock管道，可快速有效地进行脱靶识别和药物再利用。我们的方法基于蛋白质结合位点的结构和化学性质，即GRID分子相互作用域（MIF）中编码的配体图像。通过BioGPS算法，根据聚类的口袋测量口袋的重叠程度，可以揭示蛋白质的相似性。共结晶的和已知的配体可以在相似的靶标之间交叉对接，选择用于后续的体外结合实验，并且可能会提高抑制效力。我们使用人类胸苷酸合酶（TS）作为测试案例，并在整个RCSB蛋白质数据库（PDB）中搜索了类似的目标口袋。我们选择酪蛋白激酶IIalpha作为对照，并测试了其一系列针对TS模板的抑制剂。确定了鞣花酸和芹菜素为TS抑制剂，并在第二轮筛选中选择并合成了各种类黄酮。已证明这些化合物在低微摩尔范围内具有活性。
• Microbial Metabolism. Part 12.
  作者：Julie Rakel Mikell、Wimal Herath、Ikhlas Ahmad Khan

  DOI：10.1248/cpb.59.692

  日期：——

  Fermentation of 4′-hydroxyflavanone (1) with fungal cultures, Beauveria bassiana (ATCC 13144 and ATCC 7159) yielded 6,3′,4′-trihydroxyflavanone (2), 3′,4′-dihydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (3), 4′-hydroxyflavanone 3′-sulfate (4), 6,4′-dihydroxyflavanone 3′-sulfate (5) and 4′-hydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (7). B. bassiana (ATCC 13144) and B. bassiana (ATCC 7159) in addition, gave one more metabolite each, namely, flavanone 4′-O-β-D-4-methoxyglucopyranoside (6) and 6,4′-dihydroxyflavanone (8) respectively. Cunninghamella echinulata (ATCC 9244) transformed 1 to 6,4′-dihydroxyflavanone (8), flavanone-4′-O-β-D-glucopyranoside (9), 3′-hydroxyflavanone 4′-sulfate (10), 3′,4′-dihydroxyflavanone (11) and 4′-hydroxyflavanone-3′-O-β-D-glucopyranoside (12). Mucor ramannianus (ATCC 9628) metabolized 1 to 2,4-trans-4′-hydroxyflavan-4-ol (13), 2,4-cis-4′-hydroxyflavan-4-ol (14), 2,4-trans-3′,4′-dihydroxyflavan-4-ol (15), 2,4-cis-3′,4′-dihydroxyflavan-4-ol (16), 2,4-trans-3′-hydroxy-4′-methoxyflavan-4-ol (17), flavanone 4′-O-α-D-6-deoxyallopyranoside (18) and 2,4-cis-4-hydroxyflavanone 4′-O-α-D-6-deoxyallopyranoside (19). Metabolites 13 and 14 were also produced by Ramichloridium anceps (ATCC 15672). The former was also produced by C. echinulata. Structures of the metabolic products were elucidated by means of spectroscopic data. None of the metabolites tested showed antibacterial, antifungal and antiprotozoal activities against selected organisms.

  用真菌培养物白僵菌（ATCC 13144 和 ATCC 7159）发酵 4'-羟基黄烷酮 (1)，产生 6,3',4'-三羟基黄烷酮 (2)、3',4'-二羟基黄烷酮 6-O-β-<小>D-4-甲氧基吡喃葡萄糖苷 (3), 4′-羟基黄烷酮3'-硫酸酯 (4)、6,4'-二羟基黄烷酮 3'-硫酸酯 (5) 和 4'-羟基黄烷酮 6-O-β-<小>D-4-甲氧基吡喃葡萄糖苷 (7)。此外，B. bassiana (ATCC 13144) 和 B. bassiana (ATCC 7159) 各产生一种代谢物，即黄烷酮 4'-O-β-D-4-methoxyglucopyranoside (6) 和分别为 6,4'-二羟基黄烷酮 (8)。 Cunninghamella echinulata (ATCC 9244) 将 1 转化为 6,4'-二羟基黄烷酮 (8)、flavanone-4'-O-β-D-吡喃葡萄糖苷 (9)、3'-羟基黄烷酮 4'-硫酸盐(10)、3',4'-二羟基黄烷酮 (11) 和4'-羟基黄烷酮-3'-O-β-<小>D-吡喃葡萄糖苷 (12)。拉曼毛霉 (ATCC 9628) 将 1 代谢为 2,4-反式-4'-羟基黄烷-4-醇 (13)、2,4-顺式-4'-羟基黄烷-4-醇 (14)、2,4-反式-3′,4′-二羟基黄烷-4-醇 (15), 2,4-顺式-3′,4′-二羟基黄烷-4-醇(16)、2,4-反式-3′-羟基-4′-甲氧基黄烷-4-醇(17)、黄烷酮4′-O-α-<小>D-6-脱氧吡喃糖苷(18)和 2,4-顺-4-羟基黄烷酮 4'-O-α-<小>D-6-脱氧吡喃糖苷 (19)。代谢物 13 和 14 也由雷米氯铵 (ATCC 15672) 产生。前者也是由 C. echinulata 产生的。通过光谱数据阐明代谢产物的结构。测试的代谢物均未表现出针对选定生物体的抗菌、抗真菌和抗原虫活性。
• Chroman-4-One Derivatives Targeting Pteridine Reductase 1 and Showing Anti-Parasitic Activity
  作者：Flavio Di Pisa、Giacomo Landi、Lucia Dello Iacono、Cecilia Pozzi、Chiara Borsari、Stefania Ferrari、Matteo Santucci、Nuno Santarem、Anabela Cordeiro-da-Silva、Carolina Moraes、Laura Alcantara、Vanessa Fontana、Lucio Freitas-Junior、Sheraz Gul、Maria Kuzikov、Birte Behrens、Ina Pöhner、Rebecca Wade、Maria Costi、Stefano Mangani

  DOI：10.3390/molecules22030426

  日期：——

  Flavonoids have previously been identified as antiparasitic agents and pteridine reductase 1 (PTR1) inhibitors. Herein, we focus our attention on the chroman-4-one scaffold. Three chroman-4-one analogues (1-3) of previously published chromen-4-one derivatives were synthesized and biologically evaluated against parasitic enzymes (Trypanosoma brucei PTR1-TbPTR1 and Leishmania major-LmPTR1) and parasites

  黄酮类化合物以前已被确定为抗寄生虫药和蝶啶还原酶1（PTR1）抑制剂。在本文中，我们将注意力集中在苯并吡喃-4-酮支架上。合成了先前发表的chromen-4-one衍生物的三个chroman-4-one类似物（1-3），并针对寄生酶（布鲁氏锥虫（Trypanosoma brucei）PTR1-TbPTR1和Leishmania major-LmPTR1）和寄生虫（Trypanosoma brucei和Leishmania infantum）进行了生物学评估。 。解析了与化合物1配合的TbPTR1的晶体结构和LmPTR1-黄酮配合物（化合物1和3）的第一晶体结构。通过比较所观察到的和预测的化合物结合模式来解释苯并吡喃-4-酮和苯并-4-酮衍生物的抑制活性。化合物1显示出针对目标酶和寄生虫的活性，选择性指数大于7且毒性低。我们的结果为进一步的支架优化和基于结构的药物设计提供了基础，该药物设计旨
• The Constitution of Natural Tannins. VI.¹ Coloring Matters Derived from 2,5-Dihydroxyacetophenone
  作者：Alfred. Russell、Samuel Friend. Clark

  DOI：10.1021/ja01265a021

  日期：1939.10.1
• A novel Synthesis of Naringenin and Related Flavanones
  作者：Wei Cui、Ji Zhang、Qian Wang、Kai Gao、Wei Zhang、Jian Yang

  DOI：10.3184/174751914x14145820775908

  日期：2014.11

  Efficient methods are reported for the preparation of naringenin (4′,5,7-trihydroxyflavanone) which could be easily scaled-up. They have been applied to three other flavanones (6-hydroxyflavanone, 6,4′-dihydroxyflavanone, 6,3′,4′-trihydroxyflavanone) suitably.

  报告了制备柚皮素（4′,5,7-三羟基黄烷酮）的高效方法，该方法易于推广。这些方法还适用于其他三种黄烷酮（6-羟基黄烷酮、6,4′-二羟基黄烷酮、6,3′,4′-三羟基黄烷酮）。