Bonducellin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: Bonducellin
• 英文别名: (E)-7-hydroxy-3-(4-methoxybenzylidene)chroman-4-one；(3E)-7-hydroxy-3-[(4-methoxyphenyl)methylidene]chromen-4-one
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: DLQSYZMPSWHYMW-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Bonducellin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2,3-二氢-7-羟基-3-[(4-甲氧基苯基)甲基]-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Inhibition of cholinesterase and monoamine oxidase-B activity by Tacrine–Homoisoflavonoid hybrids

  摘要：

  A series of Tacrine-Homoisoflavonoid hybrids were designed, synthesised and evaluated as inhibitors of cholinesterases (ChEs) and human monoamine oxidases (MAOs). Most of the compounds were found to be potent against both ChEs and MAO-B. Among these hybrids, compound 8b, with a 6 carbon linker between tacrine and (E)-7-hydroxy-3-(4-methoxybenzylidene)chroman-4-one, proved to be the most potent against AChE and MAO-B with IC50 values of 67.9 nM and 0.401 mu M, respectively. This compound was observed to cross the blood-brain barrier (BBB) in a parallel artificial membrane permeation assay for the BBB (PAMPA-BBB). The results indicated that compound 8b is an excellent multifunctional promising compound for development of novel drugs for Alzheimer's disease (AD). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.050
• 作为产物：
  描述：

  3-氯-1-(2,4-二羟基苯基)丙烷-1-酮 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 26.0h， 生成 Bonducellin
  参考文献：
  名称：

  Noyori–Ikariya Ru（II）配合物催化亚芳基取代的色酮和四酮的不对称转移加氢：一键还原C═C和C═O键

  摘要：

  在2和3的存在下，通过C andC和C oneO一锅还原，将3-Arylidenechroman-4-ones和2-芳基-1-四氢萘酮在dr和er中以高达99：1的比例氢化为顺式苄醇。在不对称转移氢化动力学动力学拆分（ATH-DKR）条件下，Noyori–Ikariya型Ru II手性配合物和HCO 2 Na的含量为5 mol％。这些底物的氧化导致天然高纯异黄烷酮二氢bonducellin及其碳水化合物类似物的对映选择性合成。

  DOI：

  10.1021/acs.joc.0c02981

文献信息

• Part 148 in the Series “Studies on Novel Synthetic Methodologies:” Selective Acetylation of Alcohols, Phenols and Amines and Selective Deprotection of Aromatic Acetates using Silica-Supported Phosphomolybdic Acid
  作者：Biswanath Das、Ponnaboina Thirupathi、Rathod Aravind Kumar、Keetha Laxminarayana

  DOI：10.1002/adsc.200700292

  日期：2007.12.10

  efficient catalyst for the selective acetylation of alcohols, phenols and amines in the absence of any solvent and also for the chemoselective deprotection of aromatic acetates under very mild conditions. This method has been used for the protection of the hydroxy groups as well as for the deprotection of the acetates of several naturally occurring bioactive phenolic compounds. The catalyst can be easily

  发现环保的二氧化硅负载的磷钼酸是在没有任何溶剂的情况下用于醇，酚和胺的选择性乙酰化以及在非常温和的条件下用于芳族乙酸酯的化学选择性脱保护的高效催化剂。该方法已用于保护羟基以及几种天然存在的生物活性酚类化合物的乙酸酯的脱保护。该催化剂可以容易地回收和再利用。
• Isolation, Synthesis, and Bioactivity of Homoisoflavonoids from Caesalpinia pulcherrima
  作者：Biswanath Das、Ponnaboina Thirupathi、Bommena Ravikanth、Rathod Aravind Kumar、Akella Venkata Subramanya Sarma、Shaik Jilani Basha

  DOI：10.1248/cpb.57.1139

  日期：——

  One new homoisoflavonoid, (3E)-2,3-dihydro-6,7-dimethoxy-3[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and four naturally new analogues, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-methoxy-4H-1-benzopyran-4-one, (3E)-2,3-dihydro-7-hydroxy-3-[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and (3E)-2,3-dihydro-3-[(3,4-dimethoxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one, along with four known homoisoflavonoids, bonducellin, sappanone A, 2′-methoxybonducellin and 7-O-methylbonducellin were isolated from aerial parts of Caesalpinia pulcherrima. The structures of the new compounds were elucidated by interpretation of their 1D and 2D NMR spectra. Syntheses of the naturally new compounds and the known compounds have also been accomplished. The antibacterial and antifungal activities of the isolated homoisoflavonoids were studied.

  一种新的同异黄酮，(3E)-2,3-二氢-6,7-二甲氧基-3[(3-羟基-4-甲氧基苯基)亚甲基]-4H-1-苯并吡喃-4-酮和四种天然新类似物，(3E)-3-(1、3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-methoxy-4H-1-benzopyran-4-one, (3E)-2,3-羟基-3-[(3-羟基-4-甲氧基苯基)亚甲基]-4H-1-苯并吡喃-4-酮和 (3E)-2,3-二氢-3-[(3,4-二甲氧基苯基)亚甲基]-7-甲氧基-4H-1-苯并吡喃-4-酮、从 Caesalpinia pulcherrima 的气生部分中分离出了 (3,3-二氢-2,3-二氢-3-[(3,4-二甲氧基苯基亚甲基]-7-甲氧基-4H-1-苯并吡喃-4-酮)，以及四种已知的同异黄酮类化合物：bonducellin、sappanone A、2′-甲氧基bonducellin 和 7-O-甲基bonducellin。通过解释这些新化合物的一维和二维核磁共振光谱，阐明了它们的结构。此外，还完成了天然新化合物和已知化合物的合成。研究了分离出的同异黄酮类化合物的抗菌和抗真菌活性。
• Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors
  作者：Koichi Takao、Marimo Yamashita、Aruki Yashiro、Yoshiaki Sugita

  DOI：10.1248/cpb.c16-00327

  日期：——

  A series of 3-benzylidene-4-chromanone derivatives (3–20) were synthesized and the structure–activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 µM; 13: EC50 14 µM; 18: EC50 13 µM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 µM; 14: IC50 25 µM; 18: IC50 28 µM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

  合成了一系列 3-亚苄基-4-色满酮衍生物（3-20），并评估了其抗氧化和抑制α-葡萄糖苷酶活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 5、13 和 18 显示出了强效的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（5：EC50 13 µM；13：EC50 14 µM；18：EC50 13 µM）。化合物 12、14 和 18 显示出较高的α-葡萄糖苷酶抑制活性（12：IC50 15 µM；14：IC50 25 µM；18：IC50 28 µM）。化合物 18 同时显示了强效的 DPPH 自由基清除活性和 α-葡萄糖苷酶抑制活性。这些数据表明，3-亚苄基-4-色满酮衍生物（如化合物 18）可作为先导化合物，用于开发具有抗氧化活性的新型α-葡萄糖苷酶抑制剂。
• Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids
  作者：Vidavalur Siddaiah、Chunduri Venkata Rao、Somepalli Venkateswarlu、Alluri V. Krishnaraju、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmc.2005.11.031

  日期：2006.4

  vitro for their inhibitory activities against 5-lipoxygenase (5-LOX) enzyme. The analog 7-hydroxy-3-[(N,N-dimethylaminophenyl)methylene]chroman-4-one was found to possess potent inhibitory activity and was comparable to that of the standard, nordihydroguiaretic acid. These results suggest that these homoisoflavonoids, with their potent antioxidant and 5-LOX inhibitory activities, may have useful applications

  在四个步骤中，从适当取代的苯酚到苯并吡喃-4-酮合成了一系列四种天然存在的异黄酮类化合物和八种类似物。根据NMR光谱数据将产物指定为E-异构体。通过光异构化将E-异构体转化为Z-异构体。E-和Z-异构体显示出明显的化学位移，质子NMR光谱中（E）和（Z）-均异类黄酮之间的差异为确定立体化学提供了一种有用的方法。通过超氧化物歧化酶（NBT）和DPPH自由基清除方法测定了异黄酮类化合物的抗氧化活性。类似物7-羟基-3-[（3,4，5-三羟基苯基）亚甲基] chroman-4-one在这两种方法中均表现出优异的活性，其次是沙酮A，并且其效力比市售抗氧化剂如BHA，BHT等高出数倍。对这些化合物的体外抑制活性进行了评估-脂氧合酶（5-LOX）酶。发现类似物7-羟基-3-[（N，N-二甲基氨基苯基）亚甲基]苯并吡喃-4-酮具有有效的抑制活性，并且与标准的去甲二氢癸二酸相当。这些结果表明，这些同型异黄
• 7-Hydroxy-(E)-3-phenylmethylene-chroman-4-one analogues as efflux pump inhibitors against Mycobacterium smegmatis mc2 155
  作者：Somendu K. Roy、Neela Kumari、Shiv Gupta、Sonika Pahwa、Hemraj Nandanwar、Sanjay M. Jachak

  DOI：10.1016/j.ejmech.2013.06.024

  日期：2013.8

  Efflux pump (EP) induces resistance in mycobacteria and hence could be explored as a new target for the discovery of anti-TB agents. In search for efflux pump inhibitors from natural products, bonducellin, a homoisoflavonoid was isolated from Caesalpinia digyna roots and evaluated for modulation and EP inhibitory activity. Bonducellin showed modulation in the MIC of EtBr by eight fold at a concentration

  外排泵（EP）在分枝杆菌中诱导耐药性，因此可以作为发现抗结核病药物的新靶标进行探索。为了从天然产物邦杜菌素中寻找外排泵抑制剂，从洋地黄（Caesalpinia digyna）根中分离了同异黄酮，并对其调制和EP抑制活性进行了评估。Bonducellin在62.5 mg / L的浓度下对EtBr的MIC表现出八倍的调节，并且还表现出显着的EP抑制活性。设计合成方案以通过在苯基亚甲基环上进行修饰来制备7-羟基-（E）-3-苯基亚甲基-苯并二氢吡喃-4-酮的类似物，并在累积和流出试验中评估合成的化合物。类似物1，7 - 11，13 - 15，17和19被认为是良好的调制器和由≥4倍在亚抑制浓度降低的EtBr的MIC。化合物8，13和17是最有效的抑制剂溴化乙锭流出在耻垢分枝杆菌MC 2 155。