(3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-4H-1-benzopyran-4-one | 61661-19-6

• 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: (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-4H-1-benzopyran-4-one
• 英文别名: (E)-3-(4-(dimethylamino)benzylidene)chroman-4-one；(E)-3-(4-dimethylamino-benzylidene)-chroman-4-one；(3E)-3-[[4-(dimethylamino)phenyl]methylidene]chromen-4-one
• CAS: 61661-19-6；61926-50-9；61926-44-1
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: LNRGWJPLWJSMSG-SDNWHVSQSA-N

物化性质

• 熔点：
  150-153 °C(Solv: methanol (67-56-1))
• 沸点：
  475.8±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-二硫-2,5-二醇 、 (3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-4H-1-benzopyran-4-one 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.67h， 以83%的产率得到(2'SR,3SR,4'SR)-2'-(4-(dimethylamino)phenyl)-4'-hydroxy-4',5'-dihydro-2'H-spiro[chromane-3,3'-thiophen]-4-one
  参考文献：
  名称：

  通过磺胺-迈克尔/醛醇多级联反应轻松合成具有三个连续立体中心的螺二氢苯并二氢吡喃酮-四氢噻吩

  摘要：

  （E）-3-芳基苯并二氢吡喃-4-酮与1，4-二噻吩-2，5-二醇的新型磺胺-迈克尔/羟醛级联反应已得到开发。此方法提供了一种新的实用的和容易的方法来4'-羟基-2'-芳基-4'，5'-二氢-2' ħ -螺[色满-3,3'-噻吩] -4-酮用三个连续高产量的立体中心。该转化是原子经济的，具有良好的至优异的非对映选择性。

  DOI：

  10.1016/j.tetlet.2014.11.026
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 对二甲氨基苯甲醛 在 哌啶 作用下， 反应 2.0h， 以51%的产率得到(3E)-2,3-dihydro-3-[(4-dimethylaminophenyl)methylene]-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

  摘要：

  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。

  DOI：

  10.1248/cpb.c16-00327

文献信息

• 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。
• Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds
  作者：Arto Valkonen、Katri Laihia、Erkki Kolehmainen、Reijo Kauppinen、Pál Perjési

  DOI：10.1007/s11224-011-9860-6

  日期：2012.2

  (E)-3-(4′-X-benzylidene)-4-chromanones (IIIa–IIIe, X = OCH3, CH3, Cl, N(CH3)2, Br), (Z)-3-(4′-X-benzylidene)4-thiochromanones (IVa–IVd, X = Cl, Br, F, OCH3), 2-benzyl-1,2,3,4-tetrahydro-1-naphthol (V), 2-benzyl- and (E)-2-benzylidene-1-tetralones (VI and VII), and (E)-2-benzylidene-1-benzosuberol (VIII). The crystal structures have been determined for the following seven compounds: derivatives of 4-chromanones

  摘要 基于 PFG 1H、13C HMQC 和 HMBC 实验对 3-(4'-X-苄基)-4-色酮 (Ia, X = CN 和 Ib, X = NO2) 确定并分配了 1H 和 13C NMR 化学位移, 3-(4'-X-benzyl)-4-thiochromenones (IIa, X = Cl and IIb, X = Br), (E)-3-(4'-X-benzylidene)-4-chromanones (IIIa– IIIe, X = OCH3, CH3, Cl, N(CH3)2, Br), (Z)-3-(4'-X-亚苄基)4-硫代色满酮 (IVa–IVd, X = Cl, Br, F, OCH3 )、2-苄基-1,2,3,4-四氢-1-萘酚 (V)、2-苄基-和 (E)-2-亚苄基-1-四氢萘酮 (VI 和 VII)，和 (E)- 2-benzylidene-1-benzosuberol
• A facile entry into a new class of spiroheterocycles: synthesis of dispiro[oxindolechromanone/flavanone/tetralone]pyrroloisoquinoline ring systems
  作者：G Subramaniyan、R Raghunathan、M Nethaji

  DOI：10.1016/s0040-4020(02)01130-4

  日期：2002.10

  A series of novel dispiroheterocyclic systems have been synthesized by the cycloaddition of a new azomethine ylide generated by the decarboxylative route from tetrahydroisoquinoline-3-carboxylic acid and isatin with various dipolarophiles containing exocyclic double bond such as 3-arylidene-4-chromanone, 3-arylidene-4-flavanone and 2-arylidenetetrahydro-1-naphthalenone in moderate to good yield. The

  通过将由四氢异喹啉-3-羧酸和异丁烯的脱羧途径生成的新的甲亚胺基内酯与各种含环外双键的亲二氟体（如3-芳基-4-苯并二氢吡喃酮）进行环加成反应，合成了一系列新颖的双螺杂环系统。亚芳基-4-黄酮和2-芳基四氢-1-萘酮，产率中等至良好。通过单晶X射线结构和光谱技术确定标题化合物的区域和立体化学。
• Homoisoflavonoids: Natural Scaffolds with Potent and Selective Monoamine Oxidase-B Inhibition Properties
  作者：Nicoletta Desideri、Adriana Bolasco、Rossella Fioravanti、Luca Proietti Monaco、Francisco Orallo、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm1013709

  日期：2011.4.14

  A series of homoisoflavonoids [(E)-3-benzylidenechroman-4-ones la-w, 3-benzyl-4H-chromen-4-ones 2a-g, and 3-benzylchroman-4-ones 3a-e] have been synthesized and tested in vitro as inhibitors of human monoamine oxidase isoforms A and B (hMAO-A and hMAO-B). Most of the compounds were found to be potent and selective MAO-B inhibitors. In general, the (E)-3-benzylidenechroman-4-ones la-w showed activities in the nano- or micromolar range coupled with high selectivity against hMAO-B. The reduction of the exocyclic double bond results in compounds 3a-e selective against isoform B and active in the micromolar range. In contrast, the endocyclic migration of the double bond (compounds 2a-g) generally produces the loss of the inhibitory activity or a marked reduction in potency. (E)-3-(4-(Dimethylamino)benzylidene)chroman-4-one (1l) and (E)-5,7-dihydroxy-3-(4-hydroxybenzylidene)chroman-4-one (1h) were the most interesting compounds of the entire series of inhibitors, showing hMAO-B affinity better than the selective inhibitor selegiline. Molecular modeling studies have been carried out to explain the selectivity of the most active homoisoflavonoids 1h and 1l.
• Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells
  作者：Pal Perjési、Umashankar Das、Erik De Clercq、Jan Balzarini、Masame Kawase、Hiroshi Sakagami、James P. Stables、Tamas Lorand、Zsuzsanna Rozmer、Jonathan R. Dimmock

  DOI：10.1016/j.ejmech.2007.06.017

  日期：2008.4

  A series of 3-benzylidene-4-chromanones 1a-1 were prepared and their cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 lymphoid leukemia cells were compared to the previously generated biodata in these three assays for the isosteric 2-benzylidene- 1-tetralones 2a-1. Over 40% of the compounds in series 1 were more potent than their counterparts in series 2, while equipotency was noted in one-third of the comparisons made. In general the IC(50) values of 1a-1 towards the human T-lymphocytes were in the low micromolar range. Molecular modelling revealed differences in shapes of representative molecules in series 1 and 2 which may contribute to the variation in cytotoxic potencies. Most of the compounds in series 1 displayed greater potencies towards HSC-2, HSC-3, HSC-4 and HL-60 neoplasms than HGF, HPC, and HPLF normal cells and were well tolerated in mice. (c) 2007 Elsevier Masson SAS. All rights reserved.