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1. WO2020192348 - PHENYL ALLYLIDENE CYCLOHEXENONE DERIVATIVES AND PREPARATION METHOD AND USE

Publication Number WO/2020/192348
Publication Date 01.10.2020
International Application No. PCT/CN2020/076878
International Filing Date 27.02.2020
IPC
C07C 49/683 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
587Unsaturated compounds containing a keto group being part of a ring
657containing six-membered aromatic rings
683having unsaturation outside the aromatic rings
C07C 49/697 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
587Unsaturated compounds containing a keto group being part of a ring
687containing halogen
697containing six-membered aromatic rings
C07C 205/45 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
205Compounds containing nitro groups bound to a carbon skeleton
45the carbon skeleton being further substituted by at least one doubly-bound oxygen atom, not being part of a -CHO group
C07C 49/747 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
587Unsaturated compounds containing a keto group being part of a ring
703containing hydroxy groups
747containing six-membered aromatic rings
C07C 49/753 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
587Unsaturated compounds containing a keto group being part of a ring
753containing ether groups, groups, groups, or groups
C07C 225/22 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
225Compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly-bound oxygen atoms not being part of a -CHO group, e.g. amino ketones
22having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
CPC
A61P 35/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
C07C 205/45
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
205Compounds containing nitro groups bound to a carbon skeleton
45the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
C07C 225/22
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
225Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
22having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
C07C 255/40
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
255Carboxylic acid nitriles
01having cyano groups bound to acyclic carbon atoms
32having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
40the carbon skeleton being further substituted by doubly-bound oxygen atoms
C07C 2601/16
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
2601Systems containing only non-condensed rings
12with a six-membered ring
16the ring being unsaturated
C07C 49/683
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes
587Unsaturated compounds containing a keto groups being part of a ring
657containing six-membered aromatic rings
683having unsaturation outside the aromatic rings
Applicants
  • 南通大学 NANTONG UNIVERSITY [CN]/[CN]
Inventors
  • 凌勇 LING, Yong
  • 杨圣菊 YANG, Shengju
  • 张延安 ZHANG, Yan'an
  • 刘季 LIU, Ji
  • 凌长春 LING, Changchun
  • 李洋阳 LI, Yangyang
  • 刘思群 LIU, Siqun
  • 贾启新 JIA, Qixin
  • 明古旭 MING, Guxu
  • 吴红梅 WU, Hongmei
Agents
  • 南京艾普利德知识产权代理事务所(特殊普通合伙) NANJING IPLEADER INTELLECTUAL PROPERTY AGENCY FIRM
Priority Data
201910223740.422.03.2019CN
Publication Language Chinese (ZH)
Filing Language Chinese (ZH)
Designated States
Title
(EN) PHENYL ALLYLIDENE CYCLOHEXENONE DERIVATIVES AND PREPARATION METHOD AND USE
(FR) DÉRIVÉ DE PHÉNYLALLYLIDÈNE CYCLOHEXÉNONE, PROCÉDÉ DE PRÉPARATION ET UTILISATION
(ZH) 苯基亚烯丙基环己烯酮衍生物及制备方法和用途
Abstract
(EN)
Disclosed are phenyl allylidene cyclohexenone derivatives with the structure shown in general formula I. In combination with structural characteristics and structure-function relationship of piplartine, amino bonds are replaced with double bonds, and active groups are reserved, aromatic substituents are changed, novel phenyl allylidene cyclohexenone derivatives targeting thioredoxin reductase (TrxR) for tumor tissue overexpression are designed, the defects of multiple piplartine synthesis steps and requirement for expensive metal catalysts are overcome, and the anti-tumor activity of the compounds is improved. Research results indicate that the compounds have strong inhabitation effects on proliferation of tumor cells and can significantly increase the ROS level in the tumor cells and enhance the anti-tumor effect thereof.
(FR)
L'invention concerne des dérivés de phénylallylidène cyclohexénone ayant la structure représentée dans la formule générale I. L'invention utilise une combinaison avec des caractéristiques structurales et une relation structure-fonction de piplartine, le remplacement des liaisons amino par des liaisons doubles, et la réservation de groupes actifs, ce qui permet de modifier des substituants aromatiques, et de concevoir de nouveaux dérivés de phénylallylidène cyclohexénone ciblant la thiorédoxine réductase (TrxR) pour la surexpression de tissu tumoral. L'invention permet de résoudre des problèmes se rapportant à des défauts de multiples étapes de synthèse de piplartine et une exigence pour des catalyseurs métalliques onéreux, l'invention permet d'améliorer en outre l'activité antitumorale des composés. Des résultats de recherche indiquent que les composés ont des effets d'inhabitation forts sur la prolifération de cellules tumorales et peuvent augmenter de manière significative le niveau ROS dans les cellules tumorales et améliorer leur effet antitumoral.
(ZH)
本发明公开了一类苯基亚烯丙基环己烯酮衍生物,具有通式Ⅰ所示结构,本发明结合荜茇明碱的结构特点和构效关系,将酰胺键替换为双键,同时保留活性基团,改变芳环取代基,设计了靶向肿瘤组织高表达的硫氧还蛋白还原酶(TrxR)的新型苯基亚烯丙基环己烯酮类衍生物,克服了荜茇明碱合成步骤多,需昂贵的金属催化剂的缺点,提高了该类化合物的抗肿瘤活性。研究结果表明,本发明所述化合物对多种肿瘤细胞增殖都具有强烈的抑制效果,并能够显著提升其肿瘤细胞内ROS水平,增强其抗肿瘤效果。
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