5,7-dimethoxy-2-phenylchroman-4-one (4-nitrophenyl)hydrazone | 851606-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5,7-dimethoxy-2-phenylchroman-4-one (4-nitrophenyl)hydrazone
• 英文别名: N-[(5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-ylidene)amino]-4-nitroaniline
• CAS: 851606-11-6
• 化学式: C₂₃H₂₁N₃O₅
• 分子量: 419.437
• InChiKey: LGVFEZOWABAXMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 5,7-dimethoxy-2-phenylchroman-4-one (4-nitrophenyl)hydrazone 在 氯化亚砜 作用下， 反应 1.0h， 以52%的产率得到6-Chloro-2-(2-chloro-4-nitrophenyl)-4-(4-chlorophenyl)-3a,4,7,9-tetramethoxychromeno[4,3-d]thiadiazole
  参考文献：
  名称：

  Synthesis and anticancer activity of a novel class of flavonoids: 2,4-Diarylchromane[4,3-d]-Δ1,9b-1,2,3-thiadiazolines

  摘要：

  A series of 2,4-diarylchromane[4,3-d]-Delta(1.9b)-1,2,3-thiadiazolines have been synthesized by cyclization of corresponding 2-arylchroman-4-one-arylhydrazones with SOCl2 then treated with alcohol. All the compounds have been tested for their antiproliferative activity in vitro against six human tumor cell lines, and the highly potent derivative 11a exhibited in vivo inhibitory effect on tumor growth. Mechanism research indicated that it is due to 11a that induces DNA fragmentation. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.004
• 作为产物：
  描述：

  4-硝基苯肼 、 5,7-二甲氧基磺烷酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以89%的产率得到5,7-dimethoxy-2-phenylchroman-4-one (4-nitrophenyl)hydrazone
  参考文献：
  名称：

  Synthesis and anticancer activity of a novel class of flavonoids: 2,4-Diarylchromane[4,3-d]-Δ1,9b-1,2,3-thiadiazolines

  摘要：

  A series of 2,4-diarylchromane[4,3-d]-Delta(1.9b)-1,2,3-thiadiazolines have been synthesized by cyclization of corresponding 2-arylchroman-4-one-arylhydrazones with SOCl2 then treated with alcohol. All the compounds have been tested for their antiproliferative activity in vitro against six human tumor cell lines, and the highly potent derivative 11a exhibited in vivo inhibitory effect on tumor growth. Mechanism research indicated that it is due to 11a that induces DNA fragmentation. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.004

文献信息

• Synthesis of 4-Aryl-3,4-dihydro- and 2,4-Diaryl-2,3,3a,4-tetrahydrochromeno[3,4-<i>d</i>][1,2,3]diazaphospholes
  作者：Yongzhou Hu、Huazhou Ying、Yongjian Fan、Tao Liu

  DOI：10.1055/s-2007-986666

  日期：2007.10

  Reaction of 2-arylchromone-4-semicarbazones with POCl3 in the presence of SOCl2, followed by treatment with EtOH or MeOH gave 4-aryl-3,4-dihydrochromeno[3,4-d][1,2,3]diazaphospholes. Likewise, 2,4-diaryl-2,3,3a,4-tetrahydro-chromeno[3,4-d][1,2,3]diazaphospholes were obtained from 2-­phenylchromone-4-arylhydrazones.

  在 SOCl2 存在下，2-芳基色酮-4-氨基羰基与 POCl3 反应，然后用 EtOH 或 MeOH 处理，得到 4-芳基-3,4-二氢苯并吡喃并[3,4-d][1,2,3]二氮杂磷。同样，从 2-苯基色酮-4-芳基肼中也得到了 2,4-二芳基-2,3,3a,4-四氢铬并[3,4-d][1,2,3]二氮磷酸盐。