α-Cyan-3,4,5-trimethoxyzimtsaeureamid | 42864-53-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: α-Cyan-3,4,5-trimethoxyzimtsaeureamid
• 英文别名: alpha-Cyano-3,4,5-trimethoxy-cinnamamide；2-cyano-3-(3,4,5-trimethoxyphenyl)prop-2-enamide
• CAS: 42864-53-9
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: SULXVPFOQLMBGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  α-Cyan-3,4,5-trimethoxyzimtsaeureamid 在 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.08h， 生成 3-amino-2-(4-methoxybenzoyl)-6-methyl-4-(3,4,5-trimethoxyphenyl)furo[2,3-b]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Thieno[2,3-b]pyridines—A new class of multidrug resistance (MDR) modulators

  摘要：

  To identify new potent multidrug resistance modulators, we have synthesized a series of novel thieno[ 2,3-b]pyridines and furo[2,3-b] pyridines, and examined their stucture-activity relationships. All synthesized compounds were tested to determine BCRP1, P-gp, and MRP1 inhibitor activity, and most potent MDR modulators were also screened for their toxicity, cytotoxicity and Ca2+ channel antagonist activity. Among these compounds, thieno[2,3-b] pyridine (6r) was found to exhibit a potent P-gp inhibitory action with EC50 = 0.3 +/- 0.2 mu M, MRP1 inhibitory action with EC50 = 1.1 +/- 0.1 mu M and BCRP1 inhibitory action with EC50 = 0.2 +/- 0.05 mu M and may represent suitable candidate for further pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.023
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 氰乙酰胺 、 哌啶 在 异丙醇 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以to yield 123.6 g (92.5%) of α-cyano-3,4,5-trimethoxy-cinnamamide的产率得到α-Cyan-3,4,5-trimethoxyzimtsaeureamid
  参考文献：
  名称：

  Floribunda rose plant named ‘WEKfawibyblu’

  摘要：

  一种适合花园装饰的新型Floribunda玫瑰，花朵为紫红色，反面颜色较浅。

  公开号：

  USPP029467P3

文献信息

• Anticancer activities of some newly synthesized pyridine, pyrane, and pyrimidine derivatives
  作者：Abdel-Galil E. Amr、Ashraf M. Mohamed、Salwa F. Mohamed、Nagla A. Abdel-Hafez、Abu El-Fotooh G. Hammam

  DOI：10.1016/j.bmc.2006.04.045

  日期：2006.8

  A series of pyridine, pyrane, and pyrimidine derivatives (2-11) were newly synthesized using nitrobenzosuberone 1 as a starting material. The antitumor activities of the synthesized compounds were evaluated utilizing 59 different human tumor cell lines, representing leukemia, melanoma, lung, colon, brain, ovary, breast, prostate as well as kidney. Some of the tested compounds especially 2, 3, 4c, 6

  以硝基苯并亚砜1为起始原料，新合成了一系列吡啶，吡喃和嘧啶衍生物（2-11）。利用代表白血病，黑素瘤，肺，结肠，脑，卵巢，乳腺，前列腺和肾脏的59种不同的人类肿瘤细胞系评估了合成化合物的抗肿瘤活性。一些测试的化合物，特别是2、3、4c，6、7、9b，10a和11在低浓度下对所用的人类肿瘤细胞表现出更好的体外抗肿瘤活性（log（10）GI（50）= -4.7）线。另外，化合物3、4c，6、7和9b具有高度选择性来抑制白血病细胞系。报道了合成化合物的详细合成，光谱数据和抗肿瘤性质。
• Chemistry of Seven-Membered Heterocycles, VI. Synthesis of Novel Bicyclic Heterocyclic Compounds as Potential Anticancer and Anti-HIV Agents
  作者：Abou Elfatooh G. Hammam、Nagla A. Abd El-hafeza、Wanda H. Midurab、Marian Mikołajczyk

  DOI：10.1515/znb-2000-0511

  日期：2000.5.1

  arylmethylenecyanoacetamide. The synthesis of the fused-ring pyranes 8 and 9 involved the condensation of the ketones 4 and 5 with malononitrile under basic conditions. The rearrangement of 8 under acidic conditions gave the tetrahydropyridine 10. The pyran 20 was obtained from 15 and benzaldehyde. The screening tests showed that many of the compounds obtained exhibit good anticancer activity comparable to

  合成了几种新的吡啶、吡啶酮和吡喃与苯并硫杂环或苯并庚烯环稠合，作为潜在的抗癌和抗 HIV 药物。稠环吡啶 6、7 和 17-19 是通过七元环酮 1、2 和 3 与亚芳基丙二腈反应并分别用芳香醛处理亚基丙二腈 14、15 和 16 获得的. 相应的吡啶酮 11、12 和 13 由酮 1、2 和 3 和芳基亚甲基氰基乙酰胺制备。稠环吡喃 8 和 9 的合成涉及酮 4 和 5 与丙二腈在碱性条件下的缩合。8在酸性条件下重排得到四氢吡啶10。吡喃20由15和苯甲醛得到。
• Hammam, Abou El-Fotooh G.; Fahmy; Amr, Abdel-Galil E., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 8, p. 1985 - 1993
  作者：Hammam, Abou El-Fotooh G.、Fahmy、Amr, Abdel-Galil E.、Mohamed, Ashraf M.

  DOI：——

  日期：——
• Thieno[2,3-b]pyridines—A new class of multidrug resistance (MDR) modulators
  作者：Aivars Krauze、Signe Grinberga、Laura Krasnova、Ilze Adlere、Elina Sokolova、Ilona Domracheva、Irina Shestakova、Zigmars Andzans、Gunars Duburs

  DOI：10.1016/j.bmc.2014.09.023

  日期：2014.11

  To identify new potent multidrug resistance modulators, we have synthesized a series of novel thieno[ 2,3-b]pyridines and furo[2,3-b] pyridines, and examined their stucture-activity relationships. All synthesized compounds were tested to determine BCRP1, P-gp, and MRP1 inhibitor activity, and most potent MDR modulators were also screened for their toxicity, cytotoxicity and Ca2+ channel antagonist activity. Among these compounds, thieno[2,3-b] pyridine (6r) was found to exhibit a potent P-gp inhibitory action with EC50 = 0.3 +/- 0.2 mu M, MRP1 inhibitory action with EC50 = 1.1 +/- 0.1 mu M and BCRP1 inhibitory action with EC50 = 0.2 +/- 0.05 mu M and may represent suitable candidate for further pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.
• Floribunda rose plant named ‘WEKfawibyblu’
  申请人：Early Morning LLC

  公开号：USPP029467P3

  公开（公告）日：2018-07-10

  A new variety of Floribunda rose suitable for garden decoration, having flowers of fuchsia pink with lighter reverse coloration.

  一种适合花园装饰的新型Floribunda玫瑰，花朵为紫红色，反面颜色较浅。