1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-(3-nitrophenyl)-1H-pyrazole-5-carboxylic acid | 1257427-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-(3-nitrophenyl)-1H-pyrazole-5-carboxylic acid
• 英文别名: 2-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-5-(3-nitrophenyl)pyrazole-3-carboxylic acid
• CAS: 1257427-54-5
• 化学式: C₂₅H₂₀N₄O₆
• 分子量: 472.457
• InChiKey: IJADQMRMZYBTRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 3-(3-nitrophenyl)-1H-pyrazole-5-carboxylate 、 4-环氧丙烷氧基咔唑 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 32.0h， 以73%的产率得到1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-(3-nitrophenyl)-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of 1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-aryl-1H-pyrazole-5-carboxylic acid derivatives

  摘要：

  Several novel molecules, 1-(3'-(9H-carbazol-4-yloxy)-2'-hydroxypropyl)-3-aryl-1H-pyrazole-5-carboxylic acid derivatives 3a-g were synthesized and screened to evaluate their cytotoxicity against cancer cells in vitro. The compounds 3a-g has been prepared by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 4-oxiranylmethoxy-9H-carbazole in moderate to excellent yields. The cytotoxicity of synthesized compounds was evaluated by a SRB (sulforhodamine B) assay against cancer cell such as SK-N-SH human neuroblastoma (NB), human A549 lung carcinoma, human breast cancer MCF-7 cell lines. The results showed that seven compounds can suppress SK-N-SH tumor cancer cell growth. Among them, compound 3d was the most effective small molecule in inhibiting SK-N-SH cell growth. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.004

文献信息

• Synthesis and cytotoxicity evaluation of 1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-aryl-1H-pyrazole-5-carboxylic acid derivatives
  作者：Lingaiah Nagarapu、Hanmant K. Gaikwad、Kartheeka Sarikonda、Jhansi Mateti、Rajashaker Bantu、P.S. Raghu、Krishna Madhuri Manda、Shasi Vardhan Kalvendi

  DOI：10.1016/j.ejmech.2010.07.004

  日期：2010.11

  Several novel molecules, 1-(3'-(9H-carbazol-4-yloxy)-2'-hydroxypropyl)-3-aryl-1H-pyrazole-5-carboxylic acid derivatives 3a-g were synthesized and screened to evaluate their cytotoxicity against cancer cells in vitro. The compounds 3a-g has been prepared by the reaction of ethyl 3-aryl-1H-pyrazole-5-carboxylate with 4-oxiranylmethoxy-9H-carbazole in moderate to excellent yields. The cytotoxicity of synthesized compounds was evaluated by a SRB (sulforhodamine B) assay against cancer cell such as SK-N-SH human neuroblastoma (NB), human A549 lung carcinoma, human breast cancer MCF-7 cell lines. The results showed that seven compounds can suppress SK-N-SH tumor cancer cell growth. Among them, compound 3d was the most effective small molecule in inhibiting SK-N-SH cell growth. (C) 2010 Elsevier Masson SAS. All rights reserved.