cudraflavone B | 19275-49-1

• 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: cudraflavone B
• 英文别名: Mulberrochromen；cudraflavone；8-(2,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
• CAS: 19275-49-1
• 化学式: C₂₅H₂₄O₆
• 分子量: 420.462
• InChiKey: XIWCDUHPYMOFIL-UHFFFAOYSA-N

物化性质

• 熔点：
  232-235 °C
• 沸点：
  638.5±55.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-[5-hydroxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-6-oxo-2H,6H-pyrano[3,2-g]chromen-8-yl]-1,3-phenylene dibenzoate 在 乙醇 、 水 、 potassium hydroxide 作用下， 反应 0.5h， 以82%的产率得到cudraflavone B
  参考文献：
  名称：

  新环桑菌素及相关黄酮的全合成及抗菌评价

  摘要：

  Neocyclomorusin ( 1 ) 是一种天然生物活性吡喃黄酮，主要从桑科植物中分离出来，通过 Friedel-Crafts 反应、Baker-Venkataraman (BK-VK) 重排、选择性环氧化和新型 S 首次合成。N 2 型环化为关键步骤。本方案还成功应用于氧异环整合素（2）的全合成。还制备了结构相关的天然产物morusin ( 23 ) 和cudraflavone B ( 24 )。我们研究了这些天然化合物对革兰氏阴性和革兰氏阳性菌株的抗菌活性。异戊二烯化黄酮桑黄素 ( 23 ) 和 cudraflavone B ( 24 ) 的抗金黄色葡萄球菌活性与氨苄青霉素和卡那霉素 A 相当。Morusin ( 23 ) 和cudraflavone B ( 24 ) 对革兰氏阳性菌表皮葡萄球菌和枯草芽孢杆菌均表现出比氨苄西林更好的抗菌活性。新环桑素 ( 1 ) 和氧化异环整合素

  DOI：

  10.1021/acs.jnatprod.2c00658

文献信息

• Total syntheses and antibacterial evaluations of cudraflavones A-C and related Flavones
  作者：Hongbo Dong、Li Liao、Pei Yu、Bin Long、Yufei Che、Lan Lu、Bing Xu

  DOI：10.1016/j.bioorg.2023.106764

  日期：2023.11

  The total syntheses of the natural prenylated flavones cudraflavones A–C (1–3), artoheterophyllin D (28) and artelasticin (29) are reported, along with the evaluations of their antibacterial activities. The key steps of the synthesis involved a Baker-Venkataraman rearrangement and an intramolecular cyclization for the construction of the flavone core and the regioselective formation of the pyran and

  报道了天然异戊二烯化黄酮 cudraflavones A–C ( 1 – 3 )、arthetererophyllin D ( 28 ) 和 artelasticin ( 29 ) 的全合成，以及对其抗菌活性的评估。合成的关键步骤包括 Baker-Venkataraman 重排和用于构建黄酮核心的分子内环化以及吡喃和异戊烯基支架的区域选择性形成。测试的天然黄酮1 – 3和27 – 29对金黄色葡萄球菌ATCC 29213、表皮葡萄球菌ATCC 14990、粪肠球菌ATCC 29212 和枯草芽孢杆菌ATCC 6633 表现出有效的活性，MIC 值范围为 0.125 μg/mL 至 16 μg /毫升。化合物3显示出最强的效力，MIC 值在 0.125 至 1 μg/mL 范围内，作为对抗 G +细菌感染的潜在候选物。初步作用机制研究表明，这种化合物通过破坏细菌膜的完​​整性来杀死细菌。
• COMPOSITIONS COMPRISING EXTRACTS OF APLINIA AND OTHER PLANTS FOR IMPROVING JOINT HEALTH AND TREATING ARTHRITIS
  申请人：Unigen, Inc.

  公开号：EP4100034A1

  公开（公告）日：2022-12-14
• Compositions and Methods for Regulating Homeostasis of Chondrocytes, Extracellular Matrix, Articular Cartilage, and Phenotype of Arthritis
  申请人：Unigen, Inc.

  公开号：US20220000964A1

  公开（公告）日：2022-01-06

  Medicinal plant extracts and their bioactives from Alpinia, Magnolia, Kochia and Piper /Pepper are disclosed herein in combination or alone in regulating homeostasis of chondrocytes, extracellular matrix, articular cartilage, and phenotype of arthritis that lead to enhanced anabolic functions of chondrocytes, increased renewal/rebuilding/regeneration of extracellular matrix and articular cartilage, and improved phenotype of osteoarthritis and rheumatoid arthritis.
• MRGPRX2 ANTAGONIST FOR THE TREATMENT OF PSEUDO ALLERGIC REACTIONS
  申请人：The University of Hong Kong

  公开号：US20220401435A1

  公开（公告）日：2022-12-22

  Compounds that have antiallergic and/or anti-inflammatory properties and methods of making thereof are disclosed. These compounds can block MMRGPRX2 and prevent or reduce mast cells activation. Pharmaceutical formulations in a unit dosage form suitable for the delivery of the compounds to a subject in need thereof are disclosed. The pharmaceutical formulations may include one or more active agents in addition to the compounds, such as one or more additional antiallergic and/or anti-inflammatory agents. The pharmaceutical formulation can be administered by oral administration, parenteral administration, inhalation, mucosal administration, or a combination thereof. Methods for preventing or treating pseudo allergic reactions, pseudo allergic diseases, and/or pseudo inflammatory diseases, or treating or ameliorating one or more symptoms associated with a pseudo allergic reaction, a pseudo allergic disease, and/or a pseudo inflammatory disease in a subject are also disclosed.
• [EN] COMPOSITIONS COMPRISING EXTRACTS OF APLINIA AND OTHER PLANTS FOR IMPROVING JOINT HEALTH AND TREATING ARTHRITIS<br/>[FR] COMPOSITIONS COMPRENANT DES EXTRAITS D'APLINIA ET D'AUTRES PLANTES POUR AMÉLIORER LA SANTÉ ARTICULAIRE ET TRAITER L'ARTHRITE
  申请人：UNIGEN INC

  公开号：WO2021159042A1

  公开（公告）日：2021-08-12

  Medicinal plant extracts and their bioactives from Alpinia, Magnolia, Kochia and Piper/Pepper are disclosed herein in combination or alone in regulating homeostasis of chondrocytes, extracellular matrix, articular cartilage, and phenotype of arthritis that lead to enhanced anabolic functions of chondrocytes, increased renewal/rebuilding/regeneration of extracellular matrix and articular cartilage, and improved phenotype of osteoarthritis and rheumatoid arthritis.