(E)-N'-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide | 902779-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-N'-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide
• 英文别名: 3-formylchromone-N-benzoylhydrazone；3-formylchromone benzoyl hydrazone；4-oxo-4H-chromene-3-carboxaldehyde-isonicotinylhydrazone；N'-[(E)-(4-oxo-4H-chromen-3-yl)methylidene]benzenecarbohydrazide；N-[(E)-(4-oxochromen-3-yl)methylideneamino]benzamide
• CAS: 902779-63-9
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: KZWVAKKUDLOWKU-VCHYOVAHSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  9.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N'-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide 、 苯氧乙酸 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.17h， 以49%的产率得到2,3-dihydro-2-(4-oxo-4H-chromen-3-yl)-3-(2-phenoxyacetyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  3-甲酰基色酮-N-苯甲酰hydr与乙烯酮的反应。色酮1,3,4-恶二唑啉的合成与结构研究

  摘要：

  研究了由相应的酰氯2a-d和混合酸酐2e原位制备的3-甲酰基色酮-N-苯甲酰hydr与乙烯酮的反应。在所有情况下的2-（4'-氧代-4' ħ -3'-铬酰）-5-苯基-2,3-二氢-1,3,4-恶二唑（3）的产率变化，从40至80，分离％。已基于1D和2-D（COSY HH，COZY CH，COLOC CH）NMR光谱对所有产品进行了完整的结构归属。基于理论方法和实验结果，还提出了合理的反应机理。

  DOI：

  10.1002/jhet.5570440223
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 (E)-N'-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide
  参考文献：
  名称：

  色酮衍生物作为α-葡萄糖苷酶抑制剂的合成，生物学评价和分子对接研究

  摘要：

  已合成了一系列色酮衍生物4a - 4p，其特征在于1 H NMR和13 C NMR，并评估了它们 的体外α-葡萄糖苷酶抑制活性。在这些测试化合物中，有六种（4a，4b，4d，4j，4o和4p）显示出有效的α-葡萄糖苷酶抑制活性，与标准品相比，IC 50值在20.1±0.19μM至45.7±0.23μM范围内。药物阿卡波糖（IC 50  = 817.38±6.27μM）。在这个系列中，化合物4d 发现在酰肼的苯基部分带有4-磺酰胺取代基的化合物（IC 50 = 20.1±0.19μM）是活性最高的化合物。Lineweaver-Burk图分析表明，化合物4d是α-葡萄糖苷酶的非竞争性抑制剂。通过分子对接研究证实了活性最高的类似物的结合相互作用。对接研究表明4d通过氢键，芳烃-阴离子和芳烃-阳离子相互作用与残基Glu-276，Asp-214，Asp-349和Arg-439相互作用。总之，我们的研

  DOI：

  10.1016/j.bmcl.2017.05.007

文献信息

• Synthesis, Molecular Characterization, and Biological Activity of Novel Synthetic Derivatives of Chromen-4-one in Human Cancer Cells
  作者：Vivek Barve、Fakhara Ahmed、Shreelekha Adsule、Sanjeev Banerjee、Sudhir Kulkarni、Prashant Katiyar、Christopher E. Anson、Annie K. Powell、Subhash Padhye、Fazlul H. Sarkar

  DOI：10.1021/jm051068y

  日期：2006.6.1

  The synthesis and characterization of Schiff base derivatives of 3-formylchromone 3-6 (FPA-120 to FPA-123), the minimal biologically active structural motif of soy isoflavone, genistein, and their copper(II) complexes 7-10 (FPA-124 to FPA-127) are reported here. These copper complexes possess distorted square-planar geometries capable of stabilizing Cu2+/Cu+ redox forms. The molecular modeling study

  3-甲酰基色酮3-6（FPA-120至FPA-123）的席夫碱衍生物的合成和表征，大豆异黄酮，染料木黄酮及其铜（II）配合物7-10（FPA- FPA-127第124页）记录在这里。这些铜络合物具有扭曲的方形平面几何形状，能够稳定Cu2 + / Cu +氧化还原形式。分子建模研究表明，金属配合物的关键相互作用是与pleckstrin同源性（PH）和PKB（Akt）蛋白的激酶结构域中的氨基酸相互作用。铜配合物7在染料区域中比染料木黄酮显着地形成更强的电荷相互作用，从而导致活性口袋中的稳定性更好。铜配合物对激素非依赖性和转移性乳腺癌（BT20），前列腺癌（PC-3）的体外评估 和K-ras突变体（COLO 357）和K-ras野生型（BxPC-3）胰腺癌细胞揭示了7种最有效的化合物，具有PKB（Akt蛋白）抑制活性，并在孔中引起NF-kappaB失活COLO 357细胞建立的原位胰腺肿瘤模型。
• Isoflavonoid analogs and their metal complexes as anti-cancer agents
  申请人：Sarkar Fazlul

  公开号：US20070122843A1

  公开（公告）日：2007-05-31

  A pharmacologic agent for treating and/or preventing cancer, among other diseases and conditions, and particularly breast, prostate, and pancreatic cancer, in humans and animals. The novel pharmacologic agent is an isoflavonoid or isoflavonoid mimetic covalently attached to a cytotoxic pharmacophore that, preferably has the ability to conjugate with a metal salt to form a more potent metal complex, particularly a Cu(II) complex. The isoflavonoid or isoflavonoid mimetic may be non-fragmented steroidal hormone, such as progesterone which is structurally related to the isoflavone genistein, or a small molecule hormone mimetic, such as chromone. An illustrative non-fragmented steroidal embodiment is 17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenantnren-3-thiosemicarbazone and its Cu(II) complex. Effective chromone analogs include the thiosemicarbazone and hydrazone analogs of 4-oxo-4H-chromene-3-carboxaldehyde and their Cu(II) complexes.
• Isoflavonoid Analogs and their Metal Conjugates as Anti-Cancer Agents
  申请人：Fazlul Sarkar

  公开号：US20100160268A1

  公开（公告）日：2010-06-24

  A pharmacologic agent for treating and/or preventing cancer, among other diseases and conditions, and particularly breast, prostate, and pancreatic cancer, in humans and animals. The novel pharmacologic agent is an isoflavonoid or isoflavonoid mimetic covalently attached to a cytotoxic pharmacophore that, preferably has the ability to conjugate with a metal salt to form a more potent metal complex, particularly a Cu(II) complex. The isoflavonoid or isoflavonoid mimetic may he non-fragmented steroidal hormone, such as progesterone which is structurally related to the isoflavone genistein, or a small molecule hormone mimetic, such as chromone. An illustrative non-fragmented steroidal embodiment is 17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,13,14,15, 16,17-tetradecahydrocyclopenta[a]phenanthren-3-thiosemicarbazone and its Cu(II) complex. Effective chromone analogs include the thiosemicarbazone and hydrazone analogs of 4-oxo-4H-chromene-3-carboxaldehyde and their Cu(IT) complexes.
• [EN] ISOFLAVONOID ANALOGS AND THEIR METAL CONJUGATES AS ANTI-CANCER AGENTS<br/>[FR] ANALOGUES D'ISOFLAVONOÏDES ET LEURS CONJUGUÉS MÉTALLIQUES EN TANT QU'AGENTS ANTI-CANCÉREUX
  申请人：UNIV WAYNE STATE

  公开号：WO2007035927A2

  公开（公告）日：2007-03-29

  [EN] A pharmacologic agent for treating and/or preventing cancer, among other diseases and conditions, and particularly breast, prostate, and pancreatic cancer, in humans and animals. The novel pharmacologic agent is an isoflavonoid or isoflavonoid mimetic covalently attached to a cytotoxic pharmacophore that, preferably has the ability to conjugate with a metal salt to form a more potent metal complex, particularly a Cu(II) complex. The isoflavonoid or isoflavonoid mimetic may be non-fragmented steroidal hormone, such as progesterone which is structurally related to the isoflavone genistein, or a small molecule hormone mimetic, such as chromone. An illustrative non-fragmented steroidal embodiment is 17-acetyl-10,13- dimethyl- 1 ,2,6,7, 8,9, 11 , 12, 13 , 14, 15, 16, 17-tetradecahydrocyclopenta[a]phenanthren- 3-tbiosemicarbazone and its Cu(II) complex. Effective chromone analogs include the thiosemicarbazone and hydrazone analogs of 4-oxo-4H-chromene-3-carboxaldehyde and their Cu(IT) complexes.
  [FR] L'invention concerne un agent pharmacologique destiné au traitement et/ou à la prévention de du cancers entre autres pathologies et maladies, et particulièrement notamment dule cancer du pancréas, de la prostate et du sein chez des êtres humains et des animaux. Le nouvel agent pharmacologique est un isoflavonoïde ou un mimétique d'isoflavonoïde lié de manière covalente à un pharmacophore cytotoxique qui, de préférence, présente la capacité de se conjuguer à un sel métallique en vue de former un complexe métallique plus efficace, particulièrement un complexe de Cu(II). L'isoflavonoïde ou le mimétique d'isoflavonoïde peut être une hormone stéroïdienne non fragmentée, telle que la progestérone, qui, d'un point de vue structurel, est en relation avec l'isoflavone génistéine ou un petit mimétique d'une hormone moléculaireà petites molécule, tel qu'une chromone. Dans un mode de réalisation, un exemple de stéroïde non fragmenté est la 17-acétyl-10,13-diméthyl-1,2,6,7,8,9,11,12,13,14,15,16,17-tétradécahydrocyclopenta[a]phénanthrenphénanthrèn-3-thiosemicarbazone thiosémicarbazone et ses complexes de Cu(II). Des analogues efficaces de la chromone comprennent la thiosemicarbazone thiosémicarbazone et des analogues d'hydrazone de 4-oxo-4H-chromène-3-carboxaldéhyde et leurs complexes de Cu(IT).
• Synthesis, biological evaluation and molecular docking studies of chromone hydrazone derivatives as α -glucosidase inhibitors
  作者：Guangcheng Wang、Ming Chen、Jing Wang、Yaping Peng、Luyao Li、ZhenZhen Xie、Bing Deng、Shan Chen、Wenbiao Li

  DOI：10.1016/j.bmcl.2017.05.007

  日期：2017.7

  binding interactions of the most active analogs were confirmed through molecular docking studies. Docking studies showed 4d are interacting with the residues Glu-276, Asp-214, Asp-349 and Arg-439 through hydrogen bonds, arene-anion and arene-cation interactions. In summary, our studies shown that these chromone hydrazone derivatives are a new class of α-glucosidase inhibitors.

  已合成了一系列色酮衍生物4a - 4p，其特征在于1 H NMR和13 C NMR，并评估了它们 的体外α-葡萄糖苷酶抑制活性。在这些测试化合物中，有六种（4a，4b，4d，4j，4o和4p）显示出有效的α-葡萄糖苷酶抑制活性，与标准品相比，IC 50值在20.1±0.19μM至45.7±0.23μM范围内。药物阿卡波糖（IC 50  = 817.38±6.27μM）。在这个系列中，化合物4d 发现在酰肼的苯基部分带有4-磺酰胺取代基的化合物（IC 50 = 20.1±0.19μM）是活性最高的化合物。Lineweaver-Burk图分析表明，化合物4d是α-葡萄糖苷酶的非竞争性抑制剂。通过分子对接研究证实了活性最高的类似物的结合相互作用。对接研究表明4d通过氢键，芳烃-阴离子和芳烃-阳离子相互作用与残基Glu-276，Asp-214，Asp-349和Arg-439相互作用。总之，我们的研