7,2',3'-trimethoxyflavanone | 109469-73-0

• 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: 7,2',3'-trimethoxyflavanone
• 英文别名: 2',3',7-Trimethoxyflavanon；2-(2,3-dimethoxy-phenyl)-7-methoxy-chroman-4-one；2-(2,3-Dimethoxy-phenyl)-7-methoxy-chroman-4-on；2-(2,3-dimethoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 109469-73-0
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: NNKKJSANGUCFHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2'-Hydroxy-2,3,4'-trimethoxychalcone 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以50%的产率得到7,2',3'-trimethoxyflavanone
  参考文献：
  名称：

  摘要：

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

  DOI：

  10.1023/a:1014490817731

文献信息

• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.
• Arcoleo et al., Annali di Chimica, 1957, vol. 47, p. 75,80
  作者：Arcoleo et al.

  DOI：——

  日期：——
• USE OF SUBSTITUTED CHROMAN COMPOUNDS
  申请人：Instytut Biologii Medycznej Polskiej Akademii Nauk

  公开号：EP3148527A1

  公开（公告）日：2017-04-05
• [EN] USE OF SUBSTITUTED CHROMAN COMPOUNDS<br/>[FR] UTILISATION DE COMPOSÉS CHROMANE SUBSTITUÉS
  申请人：INST BIOLOG MEDYCZNEJ

  公开号：WO2015185515A1

  公开（公告）日：2015-12-10

  The invention relates to a new medicinal use of a substituted chroman compound of formula I wherein each of R1a and R1b is a substituent selected independently from the group consisting of hydrogen and phenyl optionally substituted with 1-3 substituents selected from the group consisting of halogen, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, C1- C4 alkanoyloxy, R2a and R2b are hydrogen atoms R3a and R3b is C1-C4 alkyl or R3a and R3b together represent an oxo group or together are an C5-C8 alkylene substituent so that together with the carbon atom to which R3a and R3b are attached form a ring, wherein in the main chain to C5-8 alkylene two non-adjacent carbon atoms are replaced by nitrogen atoms, and said C5-C8 alkylene is optionally substituted by a thioxo group, n is the number of the substituents Rz and is an integer from 1 to 3 inclusive, z is the sequence number of the substituent Rz and is an integer from 4 to n + 3, inclusive, (Rz) is a substituent on the benzene ring attached to a non-nodal carbon atom independently selected from the group consisting of hydroxyl, halogen, C2-C6 alkenyl, C1-C4 alkoxy, C1-4 alkanoyloxy, heterocyclic C4-C7 alkyloxy having an oxygen atom in the ring and optionally substituted with 1- 3 substituents selected from the group consisting of C1-4 alkanoyloxy, phenyl-C3-6 alkenyl optionally substituted in the aryl ring by C1-4 alkanoyloxy and substituted in the chain by an oxo group located on a carbon atom adjacent to the carbon atom involved in the double bond C = C, as tautomer, enantiomer, diastereomer, mixture of enantiomers and/or mixture of diastereomers. A compound of formula I is used as an immunosuppressive drug.