5-methoxy-8-bromo-flavanone | 92873-06-8

• 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: 5-methoxy-8-bromo-flavanone
• 英文别名: 8-bromo-5-methoxyflavanone；8-bromo-5-methoxy-2-phenyl-chroman-4-one；8-Brom-5-methoxy-flavanon；5-Methoxy-8-bromoflavanone；8-bromo-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 92873-06-8
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: PCFYWBOTVWPVDR-UHFFFAOYSA-N

物化性质

• 熔点：
  1646 °C
• 沸点：
  481.6±45.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲氧基黄烷酮 在 双氧水 、 溶剂黄146 、 sodium bromide 作用下， 反应 4.0h， 以98%的产率得到5-methoxy-8-bromo-flavanone
  参考文献：
  名称：

  Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

  摘要：

  氯化儿茶素衍生物29显示出对常见的腐生土壤和种子真菌Trichoderma koningii和Cladosporium cladosporioides具有最高活性。

  DOI：

  10.1039/c5nj00258c

文献信息

• Radical-scavenging polyphenols: new strategies for their synthesis
  作者：Paolo Bovicelli

  DOI：10.1211/jpp.59.12.0013

  日期：2010.2.18

  New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxy-tyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.

  讨论了合成多酚的新策略，这些化合物具有抗氧化性质，存在于各种植物中。采用简单和环保的方法接近了不同类别的多酚的合成，包括存在于许多自然系统中的泛醌类多酚，其中涉及电子转移机制，羟基酪醇，是橄榄中酚类分数的主要成分，以及在植物界广泛分布的类黄酮。

• Anti-mycobacterium compositions and methods of preparing and using same
  申请人：Advanced Life Sciences, Inc.

  公开号：US20040147597A1

  公开（公告）日：2004-07-29

  The present invention relates to compounds, compositions and methods for the prevention or treatment of mycobacterium infections. The compounds are naturally occurring and synthetic biflavonoids, flavonoids, chalcones and chalcone like compounds. The compounds were screened for anti-mycobacterium activity. Of the compounds showing anti-mycobacterium activity, eight were identified as particularly potent, exhibiting greater than 90% inhibition of the growth of Mtb at a concentration of 12.5 Πg/mL. The actual minimum inhibitory concentrations (MIC), defined as the lowest concentration inhibiting 99% of the inoculum, for the preferred compounds ranged from 6.8 to 48.3 ΠM. 1

  本发明涉及预防或治疗分枝杆菌感染的化合物、组合物和方法。这些化合物是天然存在和合成的双黄酮类、黄酮类、查尔酮类和查尔酮类化合物。对这些化合物进行了抗分枝杆菌活性筛选。在显示出抗霉菌活性的化合物中，有 8 种被确定为特别有效，在浓度为 12.5 Πg/mL 时，对 Mtb 生长的抑制率超过 90%。优选化合物的实际最低抑菌浓度（MIC），即抑制接种体 99% 生长的最低浓度，介于 6.8 至 48.3 ΠM 之间。 1
• [EN] ANTI-MYCOBACTERIUM COMPOSITIONS AND METHODS OF PREPARING AND USING SAME<br/>[FR] COMPOSITIONS ANTI-MYCOBACTERIUM, PROCEDES DE PREPARATION ET D'UTILISATION ASSOCIES
  申请人：ADVANCED LIFE SCIENCES INC

  公开号：WO2001021164A2

  公开（公告）日：2001-03-29

  The present invention relates to compounds, compositions and methods for the prevention or treatment of mycobacterium infections. The compounds are naturally occurring and synthetic biflavonoids, flavonoids, chalcones and chalcone like compounds. The compounds were screened for anti-mycobacterium activity. Of the compounds showing anti-mycobacterium activity, eight were identified as particularly potent, exhibiting greater than 90% inhibition of the growth of Mtb at a concentration of 12.5 νg/mL. The actual minimum inhibitory concentrations (MIC), defined as the lowest concentration inhibiting 99% of the inoculum, for the preferred compounds ranged from 6.8 to 48.3 νM.

  本发明涉及用于预防或治疗分枝杆菌感染的化合物、组合物及方法。所述化合物包括天然存在的和合成的双黄酮、黄酮、查尔酮以及类似查尔酮的化合物。这些化合物经过筛选以确定其抗分枝杆菌活性。在显示出抗分枝杆菌活性的化合物中，有八种被鉴定为特别有效，能够在12.5 µg/mL的浓度下抑制结核杆菌(Mtb)生长超过90%。这些优选化合物的实际最小抑菌浓度(MIC)，即能够抑制99%菌悬液生长的最低浓度，范围为6.8至48.3 µM。
• Selective halogenation of flavanones
  作者：Paolo Bovicelli、Roberta Bernini、Roberto Antonioletti、Enrico Mincione

  DOI：10.1016/s0040-4039(02)01117-6

  日期：2002.8

  A mild, efficient and regioselective method for the selective halogenation of flavonoids is presented. Halogenated flavanones and Flavones tire considered potential benzodiazepine receptor ligands and with DMD/NaX or oxone/acetone/water/NaX systems they can be synthesised in preparative amounts. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Chalcones and flavonoids as anti-Tuberculosis agents
  作者：Yuh-Meei Lin、Yasheen Zhou、Michael T. Flavin、Li-Ming Zhou、Weiguo Nie、Fa-Ching Chen

  DOI：10.1016/s0968-0896(02)00094-9

  日期：2002.8

  A series of flavonoids, chalcones and chalcone-like compounds were evaluated for inhibitory activity against Mycobacterium tuberculosis H37Rv. Among them, eight compounds exhibited >90% inhibition on the growth of the bacteria at a concentration of 12.5 mug/mL. Chalcones 1-(2-hydroxyphenyl)-3-(3-chlorophenyl)-2-propen-1-one (22) and 1-(2-hydroxyphenyl)-3-(3-iodophenyl)-2-propen-1-one (37) demonstrated 90 and 92% inhibition, respectively. Chalcone-like compounds (heterocyclic ring-substituted 2-propen-1-one) 1-(4-fluorophenyl)-3-(pyridin-3-yl)-2-propen-1-one (48), 1-(3-hydroxyphenyl)-3-(phenanthren-9-yl)-2-propen-1-one (49), 1-(pyridin-3-yl)-3-(phenanthen-9-yl)-2-propen-1-one (50) and 1-(furin-2-yl)-3-phenyl-2-propen-1-one (51) exhibited 98, 97, 96 and 96% inhibition, respectively. The actual minimum inhibitory concentrations (MIC), defined as the lowest concentration inhibiting 99% of the inoculum, for 22, 37, 48, 49, 50 and 51 were 20.3, 31.5, 48.3, >35.7, 6.8 and 19.2, respectively. A hydrophobic substituent on one aromatic ring, and a hydrogen-bonding group on the other aromatic ring resulted in increased anti-TB activity of the chalcones and chalcone-like compounds. Flavones and flavanones are more geometrically constrained than the corresponding chalcone analogues. The decreased activity of the flavones with respect to the chalcones may be due to the confinement of the terminal aromatic rings to the same plane. (C) 2002 Elsevier Science Ltd. All rights reserved.