(S)-2,3-dihydro-7-hydroxy-2-phenyl-4H-1-benzopyran-4-one | 2545-13-3

• 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: (S)-2,3-dihydro-7-hydroxy-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: (2S)-7-hydroxyflavan-4-one；(2S)-7-hydroxyflavanone；(-)-7-hydroxyflavanone；(S)-7-hydroxyflavanone；7-hydroxyflavanone；ddC；(2S)-7-hydroxy-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 2545-13-3
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: SWAJPHCXKPCPQZ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2,3-dihydro-7-hydroxy-2-phenyl-4H-1-benzopyran-4-one 在 NADPH disodium salt 、 口服葡萄糖 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 3,7-dihydroxyflavanone
  参考文献：
  名称：

  A Versatile Microbial System for Biosynthesis of Novel Polyphenols with Altered Estrogen Receptor Binding Activity

  摘要：

  Isoflavonoids possess enormous potential for human health with potential impact on heart disease and cancer, and some display striking affinities for steroid receptors. Synthesized primarily by legumes, isoflavonoids are present in low and variable abundance within complex mixtures, complicating efforts to assess their clinical potential. To satisfy the need for controlled, efficient, and flexible biosynthesis of isoflavonoids, a three-enzyme system has been constructed in yeast that can convert natural and synthetic flavanones into their corresponding isoflavones in practical quantities. Based on the determination of the substrate requirements of isoflavone synthase, a series of natural and nonnatural isoflavones were prepared and their binding affinities for the human estrogen receptors (ER alpha and ER beta) were determined. Structure activity relationships are suggested based on changes to binding affinities related to small variations on the isoflavone structure.

  DOI：

  10.1016/j.chembiol.2010.03.010
• 作为产物：
  描述：

  (S)-2,3-dihydro-7-(methoxymethoxy)-2-phenyl-4H-1-benzopyran-4-one 在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以88%的产率得到(S)-2,3-dihydro-7-hydroxy-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  通过铑催化的不对称1,4加成反应高效合成对黄酮类化合物，包括松果糖醇

  摘要：

  有效的合成生物活性手性黄烷酮（1）是通过Rh催化的芳基硼酸到色酮的不对称1,4-加成反应而实现的。在室温下，在0.5％Rh催化剂和贫电子手性二膦MeO-F 12 -BIPHEP的存在下，甲苯中的反应平稳进行。在该反应中，经常发生向（S）-1的1,2-加成反应生成副产物（2 S，4 R）-2,4-二芳基-4-苯并二氢呋喃，可通过改变反应溶剂来减少CH 2 Cl 2使Rh催化剂失活（需要3％）。

  DOI：

  10.1021/ol2004148

文献信息

• Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography
  作者：Gabriela Kucerova、Kveta Kalikova、Eva Tesarova

  DOI：10.1002/chir.22701

  日期：2017.6

  cellulose‐based chiral stationary phase were achieved particularly with propane‐2‐ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO2, respectively. Methanol and basic additive isopropylamine were preferred on amylose‐based chiral stationary phase. The complementary enantioselectivity of the cellulose‐ and amylose‐based chiral stationary phases allows separation

  使用一组52种分析物在超临界流体色谱中评估了两种基于多糖的手性固定相对手性结构多样的生物活性化合物的对映选择性。固定在2.5μm二氧化硅颗粒上的手性选择剂是纤维素或直链淀粉的三（3,5-二甲基苯基carmabate）衍生物。监测了多糖主链，不同的有机改性剂和不同的流动相添加剂对保留和对映体分离的影响。对于大多数化合物，发现了快速基线对映体分离的条件。纤维素基手性固定相的基线和部分对映体分离的成功率分别为51.9％和15.4％。使用基于直链淀粉的手性固定相，我们获得了76。被测化合物的基线对映体分离率为9％，部分对映体分离率为9.6％。尤其是使用丙烷-2-醇以及异丙胺和三氟乙酸的混合物作为有机改性剂和CO添加剂时，在基于纤维素的手性固定相上获得了最佳结果2个。在基于直链淀粉的手性固定相上，优选甲醇和碱性添加剂异丙胺。纤维素和直链淀粉基手性固定相的互补对映选择性可分离大多数经测试的结构不同的化
• Efficient HPLC enantiomer separation using a pillared homochiral metal–organic framework as a novel chiral stationary phase
  作者：Koichi Tanaka、Naoki Hotta、Shohei Nagase、Kenji Yoza

  DOI：10.1039/c6nj00090h

  日期：——

  HPLC enantioseparation of various racemates using novel pillared homochiral MOF–silica composite as chiral stationary phase has been successfully demonstrated.

  使用新型柱状纯手性 MOF-二氧化硅复合物作为手性固定相对各种外消旋物进行 HPLC 对映体分离已被成功证明。
• Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC
  作者：Jian Tang、Yuzhou Lin、Bo Yang、Jie Zhou、Weihua Tang

  DOI：10.1002/chir.22732

  日期：2017.9

  phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4‐chloro‐3‐methyl)phenylcarbamate and per(2‐chloro‐5‐methyl)phenylcarbamate β‐CD clicked CSPs (i.e., CCC4M3‐CSP and CCC2M5‐CSP). The enantioselectivity dependence on column temperature was studied in both normal‐phase and reversed‐phase mode high performance liquid chromatography

  混合的氯官能团和甲基官能团可以极大地调节苯基氨基甲酸酯环糊精（CD）咔哒手性固定相（CSP）的对映选择性。本文报道了对（4-氯-3-甲基）苯基氨基甲酸酯和（2-氯-5-甲基）苯基氨基甲酸酯β-CD裂解的CSP（即CCC4M3-CSP和CCC2M5-CSP）的比较研究。在正相和反相模式高效液相色谱（HPLC）中均研究了对映选择性对柱温的依赖性。热力学研究表明，CCC4M3-CSP与手性溶质之间可形成更强的分子间相互作用，以驱动手性分离。通过在HPLC中对17种模型外消旋物进行对映分离，进一步证明了CCC4M3-CSP的对映选择性更高。
• Molecular Characterization of a Stereoselective and Promiscuous Flavanone 3-Hydroxylase from <i>Carthamus tinctorius</i> L
  作者：Songyang Sui、Kebo Xie、Ruimingqian Guo、Jungui Dai、Lin Yang

  DOI：10.1021/acs.jafc.2c07202

  日期：2023.1.25

  However, the stereoselective catalytic mechanism and substrate promiscuity of this type of enzyme are not well understood. In this study, we identified and biochemically characterized CtF3H1, an F3H from Carthamus tinctorius, a plant used in traditional Chinese medicine that exhibits high stereoselectivity and substrate promiscuity toward structurally diverse (2S)-flavanones. Isothermal titration calorimetry

  黄烷酮 3-羟化酶 (F3Hs) 属于 2-酮戊二酸依赖性双加氧酶家族，在植物类黄酮生物合成中发挥重要作用。然而，这类酶的立体选择性催化机制和底物混杂性尚不清楚。在这项研究中，我们鉴定了 CtF3H1 并对其进行了生化表征，这是一种来自红花的 F3H，红花是一种用于中药的植物，对结构多样的 (2 S )-黄烷酮表现出高立体选择性和底物混杂性。等温滴定量热法显示 CtF3H1 与 (2 S )-黄烷酮 (2 S -naringenin) 和 (2 R )-黄烷酮 (2 R ) 表现出明显不同的结合行为-naringenin)，这些差异决定了它的立体选择性。对该酶及其底物之间结构-活性关系的研究表明，7-OH 和/或 4'-OH 是 (2 S )-黄烷酮的区域选择性和立体选择性 3-羟基化所必需的。同源建模和分子对接结合定点诱变确定了羟基化所必需的氨基酸残基。这些发现证明了 CtF3H1 在区
• Bioactive fractions and compounds from Dalbergia sissoo for the prevention or treatment of osteo-health related disorders
  申请人：Maurya Rakesh

  公开号：US10292994B2

  公开（公告）日：2019-05-21

  The present invention relates to bioactive fractions and compounds from Dalbergia sissoo for the prevention or treatment of osteo-health related disorders. The present invention relates in the field of pharmaceutical composition that provides new plant extracts, their fractions and pure compound isolated from natural sources that are useful for the prevention and/or treatment of various medical indications associated with estrogen dependent or independent diseases or syndromes or disorders preferably in the prevention or treatment of estrogen dependent or independent diseases or syndromes or disorders caused in humans and animals, and achievement of peak bone mass during skeletal growth and health in humans and animals. Particularly the present invention further relates to the processes for the preparation of biologically active extracts, fractions, and isolation of pure compounds, from Dalbergia sissoo plant from the family Fabaceae their pharmaceutically acceptable salts and compositions of the principal aspect of the present invention.

  本发明涉及用于预防或治疗骨健康相关疾病的 Dalbergia sissoo 的生物活性馏分和化合物。本发明涉及药物组合物领域，提供了新的植物提取物、其馏分和从天然来源分离的纯化合物，这些提取物、馏分和纯化合物可用于预防和/或治疗与雌激素依赖性或独立疾病或综合症或紊乱有关的各种医学指征，优选用于预防或治疗人类和动物引起的雌激素依赖性或独立疾病或综合症或紊乱，以及在人类和动物骨骼生长和健康过程中达到峰值骨量。特别是本发明进一步涉及从豆科植物Dalbergia sissoo中制备生物活性提取物、馏分和分离纯化合物的工艺，它们是本发明主要方面的药学上可接受的盐和组合物。