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Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride (1:1)

Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride (1:1)

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?名称














英文名

2,3-methylenedioxy-10,11-dimethoxy-13-methylprotoberberine chloride
英文别名
更多





?生物活性


































描述
13-Methylberberine chloride (13-Methylberberinium chloride)，黄连素类似物，具有抗脂肪和抗肿瘤活性。13-Methylberberine chloride (13-Methylberberinium chloride) 可增加 IL-12 的产生，并在 LPS 激活的巨噬细胞转录后抑制 iNOS 的表达。
相关类别




SMILES

CC1=C(C=CC(OC)=C2OC)C2=C[N+]3=C1C4=CC(OCO5)=C5C=C4CC3.[Cl-]
参考文献

[1]. Chow YL, et al. 13-Methylberberine, a berberine analogue with stronger anti-adipogenic effects on mouse 3T3-L1 cells. Sci Rep. 2016 Dec 5;6:38129.

[2]. Iwasa K, et al. In vitro cytotoxicity of the protoberberine-type alkaloids. J Nat Prod. 2001 Jul;64(7):896-8.

[3]. Lee DU, et al. Effects of 13-alkyl-substituted berberine alkaloids on the expression of COX-II, TNF-alpha, iNOS, and IL-12 production in LPS-stimulated macrophages. Life Sci. 2003 Aug 1;73(11):1401-12.






?物理化学性质






















分子式 C21H20ClNO4
分子量 385.84100
精确质量 385.10800
PSA 40.80000
LogP 0.40870





?合成线路























甲醛结构式

甲醛

50-00-0








二氢小檗碱结构式

二氢小檗碱

483-15-8




~37%







Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride (1:1)结构式

Benzo[g]-1,3-be…

54260-72-9


文献：Li, Ying-Hong; Yang, Peng; Kong, Wei-Jia; Wang, Yan-Xiang; Hu, Chang-Qin; Zuo, Zeng-Yan; Wang, Yue-Ming; Gao, Hong; Gao, Li-Mei; Feng, Yan-Chun; Du, Na-Na; Liu, Ying; Song, Dan-Qing; Jiang, Jian-Dong Journal of Medicinal Chemistry, 2009 , vol. 52, # 2 p. 492 – 501





9,10-dimethoxy-2,3-methylenedioxy-8,14-cycloberbin-13-one结构式

9,10-dimethoxy-…

80665-65-2




~%







Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride (1:1)结构式

Benzo[g]-1,3-be…

54260-72-9


文献：Hanaoka, Miyoji; Yoshida, Shuji; Mukai, Chisato Journal of the Chemical Society, Chemical Communications, 1985 , # 18 p. 1257 – 1258





9,10-dimethoxy-13-methylene-2,3-methylenedioxy-8,14-cycloberbine结构式

9,10-dimethoxy-…

100986-33-2




~80%







Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride (1:1)结构式

Benzo[g]-1,3-be…

54260-72-9


文献：Hanaoka; Yoshida; Mukai Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 12 p. 3264 – 3267





9,10-dimethoxy-13-methyl-5,6,8,13-tetrahydro-8,13a-propano-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-16-one结构式

9,10-dimethoxy-…

38699-81-9




~%







Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl-, chloride (1:1)结构式

Benzo[g]-1,3-be…

54260-72-9


文献：Naruto; Nishimura; Kaneko Chemical and Pharmaceutical Bulletin, 1975 , vol. 23, # 6 p. 1271 – 1275




















?英文别名


















dehydrothalictricavine chloride


13-Methylberberinium chlorid


13-methylberberine chloride








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