4-hydroxy-3-methoxy-benzonitrile N-oxide | 1186630-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-methoxy-benzonitrile N-oxide
• 英文别名: 4-Hydroxy-3-methoxybenzonitrile oxide；4-hydroxy-3-methoxybenzonitrile oxide
• CAS: 1186630-50-1
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: QTUBGZIYRHDVPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methoxy-benzonitrile N-oxide 、 银胶菊宁 以 四氢呋喃 为溶剂， 反应 3.33h， 以74%的产率得到(3aR,6S,6aS,9aS,9bR)-6a-hydroxy-3'-(4-hydroxy-3-methoxyphenyl)-6,9a-dimethylspiro[4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-3,5'-4H-1,2-oxazole]-2,9-dione
  参考文献：
  名称：

  [EN] SPIRO DERIVATIVES OF PARTHENIN AS NOVEL ANTICANCER AGENTS
  [FR] DÉRIVÉS SPIRO DE PARTHÉNINE SERVANT DE NOUVEAUX AGENTS ANTICANCÉREUX

  摘要：

  公开号：

  WO2009110007A8
• 作为产物：
  描述：

  vanillin oxime 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-hydroxy-3-methoxy-benzonitrile N-oxide
  参考文献：
  名称：

  Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents

  摘要：

  Several novel Spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (alpha-methylene-gamma-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of alpha,beta-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.030

文献信息

• Spiro Derivatives of Parthenin as Novel Anticancer Agents
  申请人：Halmuthur Mahabalarao Sampath Kumar

  公开号：US20110201661A1

  公开（公告）日：2011-08-18

  The present invention relates to novel spiro derivatives of parthenin prepared by the dipolar cycloaddition of various dipoles viz, benzonitrile oxides, nitrones, azides, nitrile ylide diazoalkane, nitrile imide, ozone, azomethine imides, azomethine ylides etc. with exocyclic double bond of C ring (α-methylene-γ-butyrolactone). Representative compounds have been screened for their anticancer activity against different cancer cell lines. ICs0 value of these analogues varies between 4.3 μM to 93 μM. A mechanistic correlation of their anticancer activity has been described. The results of the cytotoxicity test of the compounds studies indicated that the α,β-unsaturated ketonic moiety in parthenin plays an important role in the maintenance of the high level of cytotoxicity.
• US8609858B2
  申请人：——

  公开号：US8609858B2

  公开（公告）日：2013-12-17
• Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents
  作者：Doma Mahendhar Reddy、Naveed A. Qazi、Sanghpal D. Sawant、Abid H. Bandey、Jada Srinivas、Mannepalli Shankar、Shashank K. Singh、Monika Verma、Gousia Chashoo、Arpita Saxena、Dilip Mondhe、Ajit K. Saxena、V.K. Sethi、Subhash C. Taneja、Gulam N. Qazi、H.M. Sampath Kumar

  DOI：10.1016/j.ejmech.2011.04.030

  日期：2011.8

  Several novel Spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (alpha-methylene-gamma-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of alpha,beta-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described. (C) 2011 Elsevier Masson SAS. All rights reserved.
• [EN] SPIRO DERIVATIVES OF PARTHENIN AS NOVEL ANTICANCER AGENTS<br/>[FR] DÉRIVÉS SPIRO DE PARTHÉNINE SERVANT DE NOUVEAUX AGENTS ANTICANCÉREUX
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2009110007A8

  公开（公告）日：2010-10-21