cis-4',7-dihydroxyflavan-4-ol | 7508-30-7

• 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: cis-4',7-dihydroxyflavan-4-ol
• 英文别名: (+/-)-4'-Hydroxy-flavan-4β-ol；(2R,4R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-ol
• CAS: 7508-30-7；24272-00-2；67814-49-7；72150-58-4；105880-35-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: VIWWLMUBPMSXTF-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-4',7-dihydroxyflavan-4-ol 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 4.0h， 以16%的产率得到trans-4',7-dihydroxy-4-imidazol-1-ylflavan
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-imidazolylflavans as nonsteroidal aromatase inhibitors

  摘要：

  A series of 4-imidazolylflavans having a variety of substituents on the 2-phenyl ring was synthesized and investigated for their inhibitory effect against aromatase. Structure activity relationships of these compounds were determined. An additional chlorine atom or a cyano group at the 4' position did not enhance aromatase inhibition as well as a 3'-hydroxyl group. The influence of an additional 4'-hydroxyl group depends on the substitution pattern of A ring. Among these molecules, 4'-hydroxy-4-imidazolyl-7-methoxyflavan is only 2.2-fold less active than the letrozole (as assessed by IC50 values). Letrozole is used as the first-line therapy for metastatic breast cancer. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.06.008
• 作为产物：
  描述：

  4'-羟基黄烷酮 在 Ramichloridium anceps ATCC 15672 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 336.0h， 以12.7%的产率得到2,4-trans-4'-hydroxyflavan-4-ol
  参考文献：
  名称：

  Microbial Metabolism. Part 12.

  摘要：

  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。

  DOI：

  10.1248/cpb.59.692

文献信息

• Synthesis and biological evaluation of 4-imidazolylflavans as nonsteroidal aromatase inhibitors
  作者：Christelle Pouget、Samir Yahiaoui、Catherine Fagnere、Gerard Habrioux、Albert Jose Chulia

  DOI：10.1016/j.bioorg.2004.06.008

  日期：2004.12

  A series of 4-imidazolylflavans having a variety of substituents on the 2-phenyl ring was synthesized and investigated for their inhibitory effect against aromatase. Structure activity relationships of these compounds were determined. An additional chlorine atom or a cyano group at the 4' position did not enhance aromatase inhibition as well as a 3'-hydroxyl group. The influence of an additional 4'-hydroxyl group depends on the substitution pattern of A ring. Among these molecules, 4'-hydroxy-4-imidazolyl-7-methoxyflavan is only 2.2-fold less active than the letrozole (as assessed by IC50 values). Letrozole is used as the first-line therapy for metastatic breast cancer. (C) 2004 Elsevier Inc. All rights reserved.
• 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。