Synthesis and biological activity of heterocycle-fused derivatives of pentacylic triterpenes as glycogen phosphorylase inhibitors

WEN Xiao-an; ZHANG Ying-xia; LIU Jun; ZHANG Lu-yong; NI Pei-zhou; SUN Hong-bin

Journal of China Pharmaceutical University > 2009 > 40(6): 491-496.

WEN Xiao-an, ZHANG Ying-xia, LIU Jun, ZHANG Lu-yong, NI Pei-zhou, SUN Hong-bin. Synthesis and biological activity of heterocycle-fused derivatives of pentacylic triterpenes as glycogen phosphorylase inhibitors[J]. Journal of China Pharmaceutical University, 2009, 40(6): 491-496.

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Synthesis and biological activity of heterocycle-fused derivatives of pentacylic triterpenes as glycogen phosphorylase inhibitors

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Aim ：To search for novel modulators of glycogen metabolism through structural modifications of natural pentacyclic triterpenes. Methods ：A series of N-heterocyclic derivatives were synthesized by fusing indole，quinoxaline and pyrazine rings with A-ring of oleanolic and ursolic acids.The compounds were biologically _{evaluated for their inhibitory activity against rabbit muscle glycogen phosphorylase. Results and Conclusion ：Twelve heterocyclic triterpene derivatives were synthesized and their structures were confirmed by IR，¹H NMR，_{13C NMR and MS.Except for compound 12 ，all of the compounds exhibited glycogen phosphorylase _{inhibitory activity with IC₅₀ values in the range of 14-252 μmol/L.Among this series of compounds，compound 15 showed the best potency with IC₅₀ of 14 μmol/L.}}}

Keywords:
pentacyclic triterpene,
structural modification,
heterocyclic compounds,
glycogen phosphorylase inhibitors

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[1]	ZHAO Xiaomei, WANG Xin, JI Xia, ZHANG Hua, ZHANG Pingping, HU Guoqiang. Synthesis and antitumor activities of 1, 2-benzothiazines［1, 3, 4］thiadiazolo［3, 2-a］［1, 3, 5］triazin derivatives[J]. Journal of China Pharmaceutical University, 2020, 51(1): 24-28. DOI: 10.11665/j.issn.1000-5048.20200104
[2]	WU Mingming, FANG Lei, GOU Shaohua, CHEN Li. 以2-甲基-2-取代苯氧基丙酸为离去基团的铂(Ⅱ)配合物的合成、表征及细胞毒活性[J]. Journal of China Pharmaceutical University, 2013, 44(4): 303-306. DOI: 10.11665/j.issn.1000-5048.20130403
[3]	CAO Jin-ming, WU Yan-jun, ZHU Chong-quan, HUANG Wen-long. Synthesis and anti-virus activities of 1,2,4-oxadiazole-phenoxy alkyl-isoxazole derivatives[J]. Journal of China Pharmaceutical University, 2011, 42(4): 299-304.
[4]	Synthesis and iNOS Inhibitory Activity of 1-Alkyl(or Hydro)-3-[4-(5-Substituted Benzimidazole(or Benzothiazole) -2-Mercapto) Phenyl] Thioureas[J]. Journal of China Pharmaceutical University, 2004, (6): 6-9.
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[8]	Synthesis and Antihypertensive Activity of Ethyl-1-Substituted-2-Alkyl-4-Chloro-1,6-Dihydro-6-Methyl-5-Pyrimidinecarboxylates[J]. Journal of China Pharmaceutical University, 1999, (6): 8-12.
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Synthesis and biological activity of heterocycle-fused derivatives of pentacylic triterpenes as glycogen phosphorylase inhibitors

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