(E)-1-(4-methoxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(4-methoxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one
• 英文别名: (E)-1-(4-methoxyphenyl)-3-(3-pyridyl)prop-2-en-1-one；(E)-1-(4-methoxyphenyl)-3-pyridin-3-ylprop-2-en-1-one
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: WPXOTBIFJKUITB-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one 以53%的产率得到
  参考文献：
  名称：

  CUSSAC M.; BOUCHERLE A.; HACHE J., EUR. J. MED. CHEM., 1977, 12, NO 2, 177-181

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吡啶甲醛 、 对甲氧基苯乙酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以38%的产率得到(E)-1-(4-methoxyphenyl)-3-(3-pyridinyl)prop-2-en-1-one
  参考文献：
  名称：

  吡啶甲醛与有机碱的缩合反应

  摘要：

  DBU介导的羟醛缩合脱水序列已用于制备一系列合成上重要的取代的2-和3-氮杂十二碳烯酮。在该协议中没有观察到通常与该序列伴随无机碱的迈克尔产物，具有很高的实用价值。

  DOI：

  10.1002/adsc.200404318

文献信息

• Synthesis and antimicrobial activity of methoxy azachalcones and N-alkyl substituted methoxy azachalconium bromides
  作者：CANAN ALBAY、NURAN KAHRİMAN、NAGİHAN YILMAZ İSKENDER、ŞENGÜL ALPAY KARAOĞLU、NURETTİN YAYLI

  DOI：10.3906/kim-1007-790

  日期：——

  In this study, 18 new N-octyl, N-decyl, and N-dodecyl substituted o-, m-, and p-methoxy (E)-3- and 4-azachalcones, 4- or 3-[(1E)-3-(4-, 3-, or 2-methoxyphenyl)-3-oxoprop-1-en-1-yl]-1-alkyl (C_8,10,12}) pyridinium bromides} (1a-6a, 1b-1b, and 1c-6c), and 4 new o-, and m-methoxy (E)-3- and 4-azachalcones (2, 3, 5, and 6) were synthesized and tested for antimicrobial activities against Escherichia coli, Yersinia pseudotuberculosis, Enterobacter aerogenes, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Bacillus cereus, and Candida albicans. N-Alkyl substituted azachalconium bromides showed good antimicrobial activity against all tested microorganisms with minimal inhibitory concentration (MIC) values in the range of 0.42-58.7 \mu g/mL in most cases. Nonalkylated compounds 1-9 were not as effective as the alkylated compounds. They showed only antimicrobial activity against gram-positive bacteria and yeast in the range of 1.77-123.7 \mu g/mL. The optimum length of the alkyl chain for better activity is situated with 12 carbon atoms in the series of compounds 1a-c, 2a-c, 3a-c, 4a-c, 5a-c, and 6a-c. N-Alkyl derivatives of m-methoxy (E)-3-azachalcone (4a-c, 5a-c, and 6a-c) showed better activity in comparison to those of o- and p-methoxy (E)-4-azachalcones (1a-c, 2a-c, and 3a-c).

  在本研究中，合成了18种新的N-octyl、N-decyl和N-dodecyl取代的o-、m-和p-甲氧基(E)-3-和4-氮杂查尔酮，4或3-[(1E)-3-(4-、3-或2-甲氧基苯基)-3-氧代丙-1-烯-1-基]-1-烷基(C_8,10,12})吡啶鎓溴盐}(1a-6a，1b-1b，和1c-6c)，以及4种新的o-和m-甲氧基(E)-3-和4-氮杂查尔酮(2、3、5和6)，并对其在抗菌活性方面进行了测试，针对的微生物包括大肠杆菌、假性结核分枝杆菌、肠道气单胞菌、铜绿假单胞菌、金黄色葡萄球菌、肠球菌、蜡样芽孢杆菌和白色念珠菌。N-烷基取代的氮杂查尔酮溴化物显示出良好的抗菌活性，针对所有测试的微生物，其最小抑菌浓度(MIC)值在0.42-58.7 μg/mL范围内。在大多数情况下，未烷基化的化合物1-9的效果不如烷基化化合物。它们仅显示出对革兰阳性细菌和酵母的抗菌活性，浓度范围为1.77-123.7 μg/mL。为了获得更好的活性，烷基链的最佳长度为12个碳原子，在化合物系列1a-c、2a-c、3a-c、4a-c、5a-c和6a-c中。与o-和p-甲氧基(E)-4-氮杂查尔酮(1a-c、2a-c和3a-c)相比，m-甲氧基(E)-3-氮杂查尔酮的N-烷基衍生物(4a-c、5a-c和6a-c)显示出更好的活性。
• Organic Base-Mediated Condensation of Pyridinecarboxaldehydes to Azachalcones
  作者：Laura?E. Downs、Derek?M. Wolfe、Peter?R. Schreiner

  DOI：10.1002/adsc.200404318

  日期：2005.2

  A DBU-mediated aldol condensation-dehydration sequence has been used to prepare a series of synthetically important substituted 2- and 3-azachalcones. Michael products that typically accompany this sequence with inorganic bases were not observed in this protocol of high practical value.

  DBU介导的羟醛缩合脱水序列已用于制备一系列合成上重要的取代的2-和3-氮杂十二碳烯酮。在该协议中没有观察到通常与该序列伴随无机碱的迈克尔产物，具有很高的实用价值。
• Discovery and characterization of novel CYP1B1 inhibitors based on heterocyclic chalcones: Overcoming cisplatin resistance in CYP1B1-overexpressing lines
  作者：Neill J. Horley、Kenneth J.M. Beresford、Tarun Chawla、Glen J.P. McCann、Ketan C. Ruparelia、Linda Gatchie、Vinay R. Sonawane、Ibidapo S. Williams、Hoon L. Tan、Prashant Joshi、Sonali S. Bharate、Vikas Kumar、Sandip B. Bharate、Bhabatosh Chaudhuri

  DOI：10.1016/j.ejmech.2017.02.016

  日期：2017.3

  The structure of alpha-napthoflavone (ANF), a potent inhibitor of CYP1A1 and CYP1B1, mimics the structure of chalcones. Two potent CYP1B1 inhibitors 7k (DMU2105) and 6j (DMU2139) have been identified from two series of synthetic pyridylchalcones. They inhibit human CYP1B1 enzyme bound to yeast-derived microsomes (Sacchrosomes((TM))) with IC50 values of 10 and 9 nM, respectively, and show a very high level of selectivity towards CYP1B1 with respect to the IC50 values obtained with CYP1A1, CYP1A2, CYP3A4, CYP2D6, CYP2C9 and CYP2C19 Sacchrosomes((TM)). Both compounds also potently inhibit CYP1B1 expressed within 'live' recombinant yeast and human HEK293 kidney cells with IC50 values of 63, 65, and 4, 4 nM, respectively. Furthermore, the synthesized pyridylchalcones possess better solubility and lipophilicity values than ANF. Both compounds overcome cisplatine-resistance in HEK293 and A2780 cells which results from CYP1B1 overexpression. These potent cell-permeable and water-soluble CYP1B1 inhibitors are likely to have useful roles in the treatment of cancer, glaucoma, ischemia and obesity. (C) 2017 Elsevier Masson SAS. All rights reserved.
• US5208343A
  申请人：——

  公开号：US5208343A

  公开（公告）日：1993-05-04
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UNIV MONTFORT

  公开号：WO2015166043A1

  公开（公告）日：2015-11-05

  The invention relates to a compound of formula (I) for use in the prevention and/or treatment of cancer, wherein rings A and B are independently an optionally substituted aryl or an optionally substituted heteroaryl. The compounds are particularly provided for the prevention and/or treatment of hormone- induced cancers, such as breast, ovarian, uterine, endometrial and prostate cancer.