6,2’-dihydroxyflavanone | 19393-40-9

• 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: 6,2’-dihydroxyflavanone
• 英文别名: 6,2'-dihydroxyflavanone；6-hydroxy-2-(2-hydroxy-phenyl)-chroman-4-one；6-Hydroxy-2-(2-hydroxy-phenyl)-chroman-4-on；6-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 19393-40-9
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: JMSUEPQZGKBECJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,2’-dihydroxyflavanone 生成 (4S)-4-[(4R)-4,6-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydrochromen-4-yl]-2-(2-hydroxyphenyl)-2,3-dihydrochromene-4,6-diol
  参考文献：
  名称：

  SAHANA H. S.; TIWARI R. D., J. INDIAN CHEM. SOC. , 1976, 53, NO 5, 530-531

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 6,2’-dihydroxyflavanone
  参考文献：
  名称：

  一些黄烷酮衍生物的合成，生物学评估以及计算机代谢和毒性预测。

  摘要：

  黄酮化学上是花青素，以游离态或与单宁有关的糖苷（类黄酮）存在。类黄酮（黄酮的衍生物）具有多种药理活性，并且由于其具有黄嘌呤氧化酶抑制作用，因此还具有超氧化物清除活性。通过环化法从查耳酮合成了一系列的2-苯基-2,3-二氢色子-4-酮衍生物（黄酮衍生物），并评估了它们对某些革兰氏阳性和革兰氏阴性细菌的活性。IR，NMR和CHN分析证实了合成化合物的结构。抗菌研究的结果表明，化合物2b，2e，2f和2h具有对抗许多细菌菌株的活性。其中，化合物（2h）对所有菌株viz具有显着的活性。对金黄色葡萄球菌，S。sonnei，大肠杆菌，鼠伤寒沙门氏菌和霍乱弧菌的抑制浓度为25微克/毫升。化合物2f对大肠杆菌和鼠伤寒沙门氏菌的最低抑菌浓度为200微克/毫升，对S. sonnei，痢疾链球菌和霍乱弧菌的最小抑菌浓度为25微克/毫升。在计算机上对合成的化合物进行代谢和毒性研究，预测结果表明具有羟基官能团的化合

  DOI：

  10.1248/cpb.54.1384

文献信息

• Method for producing a heterocyclic compound and an aromatic carboxylic acid having one or more hydroxyl groups, and modified aromatic ring dioxygenase
  申请人：——

  公开号：US20040086983A1

  公开（公告）日：2004-05-06

  An objective of the present invention is to provide a method of producing hydroxylated heterocyclic compounds and hydroxylated aromatic carboxylic acids by bioengineering technique, and modified enzymes which can be used for this method. A method of producing hydroxylated heterocyclic compounds or hydroxylated aromatic carboxylic acids comprises reacting an aromatic ring dioxygenase with heterocyclic compounds or aromatic carboxylic acids to hydroxylate these compounds. An enzyme according to the present invention is an aromatic ring dioxygenase comprising an &agr;-subunit consisting of the amino acid sequence of SEQ ID NO: 2, which is modified according to the &agr;-subunit of the biphenyl dioxygenase derived from the strain Burkholderia cepacia LB400, a &bgr;-subunit consisting of the amino acid sequence of SEQ ID NO: 4, and a ferredoxin consisting of the amino acid sequence of SEQ ID NO: 6, and a ferredoxin reductase consisting of the amino acid sequence of SEQ ID NO: 8.

  本发明的目的是提供一种通过生物工程技术生产羟基化杂环化合物和羟基化芳香族羧酸的方法，以及可用于该方法的改良酶。生产羟基化杂环化合物或羟基化芳香族羧酸的方法包括使芳香环二加氧酶与杂环化合物或芳香族羧酸反应，使这些化合物羟基化。根据本发明的一种酶是一种芳香环二加氧酶，它包括一个由 SEQ ID NO: 2 的氨基酸序列组成的&agr;-亚基，它是根据从菌株中得到的联苯二加氧酶的&agr;-亚基修饰的 伯克霍尔德氏菌 LB400，由 SEQ ID NO: 4 的氨基酸序列组成的&bgr;-亚基，由 SEQ ID NO: 6 的氨基酸序列组成的铁毒素，以及由 SEQ ID NO: 8 的氨基酸序列组成的铁毒素还原酶。
• 5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer
  作者：Yohei Saito、Atsushi Mizokami、Hiroyuki Tsurimoto、Kouji Izumi、Masuo Goto、Kyoko Nakagawa-Goto

  DOI：10.1016/j.ejmech.2018.08.069

  日期：2018.9

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Vyas; Shah, Journal of the Indian Chemical Society, 1949, vol. 26, p. 273,274
  作者：Vyas、Shah

  DOI：——

  日期：——
• 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
• GANDHI P.; TIWARI R. D., J. INDIAN CHEM. SOC. <JICS-AH>, 1977, 54, NO 6, 643
  作者：GANDHI P.、 TIWARI R. D.

  DOI：——

  日期：——