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氯化两面针碱(标准品)

Nitidine chloride

CAS: 13063-04-2

Molecular Formula: C21H18NO4+

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氯化两面针碱(标准品) - Names and Identifiers

Name Nitidine chloride
Synonyms NITIDINE
Angolinine
Nitidine chloride
NITIDINE CHLORIDE (RG)
dimethoxy-12-methyl-,chloride
[1,3]Dioxolo[4,5]benzo[1,2-c]phenanthridinium, 2,3-
2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
2,3-Dimethoxy-12-methyl-(1,3)-benzodioxolo(5,6-c)phenanthridinium chloride
2,3-dimethoxy-12-methyl-3,12-dihydro[1,3]benzodioxolo[5,6-c]phenanthridine
2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium chloride
CAS 13063-04-2
EINECS 683-192-4
InChI InChI=1/C21H19NO4/c1-22-10-13-7-17(23-2)18(24-3)8-15(13)14-5-4-12-6-19-20(26-11-25-19)9-16(12)21(14)22/h4-10,18H,11H2,1-3H3
InChIKey QLDAACVSUMUMOR-UHFFFAOYSA-M

氯化两面针碱(标准品) - Physico-chemical Properties

Molecular FormulaC21H18NO4+
Molar Mass348.37
Density1.35g/cm3
Melting Point283-286 °C
Boling Point619°C at 760 mmHg
Flash Point189.4°C
Solubility Soluble in DMSO
Vapor Presure3.01E-15mmHg at 25°C
AppearancePale yellow needle crystal (methanol)
Colorwhite to beige
Storage Condition-20°C
Refractive Index1.696
MDLMFCD01659688
Physical and Chemical PropertiesIt is derived from Zanthoxylum nitidum.

氯化两面针碱(标准品) - Risk and Safety

Safety Description24/25 - Avoid contact with skin and eyes.
WGK Germany3
RTECSDF4935500
HS Code29399990

氯化两面针碱(标准品) - Reference

Reference
Show more
1. Yang Xuefen and Lu Xiaoshan. Determination of nitidine chloride in Sanjiu Weitai Granules by HPLC [J]. Chinese folk medicine 2017 26(013):25-27.
2. Lu Yi, Zhu Yuanzhang, Guo Chenxu, et al. Anti-inflammatory and analgesic effects of Feilong palm blood alcohol extract [J]. Chinese patent medicine, 2018, 040(001):26-32.
3. Tao, Y, Jiang, E, Cai, B. A biochemometrics strategy combining quantitative determination, bioactivity evaluation and relationship analysis for identification of analgesic alkaloids of raw and vinegar-processed Corydalis turtschaninovii. J Sep Sci 2020; 43
4. Tao, Yi, et al. "Establishment of a rapid and sensitive UPLC-MS/MS method for pharmacokinetic determination of nine alkaloids of crude and processed Corydalis turtschaninovii Besser aqueous extracts in rat plasma." Journal of Chromatography B 1124 (2019):
5. Tao, Y, Jiang, E, Cai, B. A biochemometrics strategy combining quantitative determination, bioactivity evaluation and relationship analysis for identification of analgesic alkaloids of raw and vinegar-processed Corydalis turtschaninovii. J Sep Sci 2020; 43

氯化两面针碱(标准品) - Reference Information

overview gastric cancer is characterized by uncontrolled cell proliferation, migration and invasion. Gastric cancer is difficult to diagnose in the early stage, and generally it has entered an advanced stage when it is diagnosed. Nanthoxylum nitidum is derived from the root of the plant Nanthoxylum nitidum and is a natural plant alkaloid. Nitidine chloride (NC) is a chloride of nitidine, which has anti-infective, anti-malarial, anti-fungal, anti-angiogenic and anti-tumor activities. NC has certain anti-tumor effect. However, few articles report the effect of NC on proliferation and migration of gastric cancer [1].
nitidine chloride (nitidine chloride,NC) is derived from Guangxi endemic medicinal plant nitidine Zanthoxylumnitidum(Roxb.)DC. The alkaloids isolated from the roots. Previous studies have confirmed that it has a variety of biological activities of anti-inflammatory, antifungal, antioxidant and anti-HIV, and because it can inhibit the proliferation of various types of tumor cells and induce tumor cell apoptosis, it has been identified as a potential anti-tumor compound [2].
optimization of synthesis process 4-1 (benzo [d][1,3] dioxolane -5-1). 2.(3,4-dimethoxyphenyl) -4-oxobutyronitrile is hydrolyzed and reduced to obtain 4-(benzo [d][1,3] dioxolane -5-group) -2-(3,4-dimethoxyphenyl) butyric acid; After Friedel reaction, Liu Carter reaction and cyclization, 2,3-methylenedioxyl -8 are obtained, 9-dimethoxy-4b,10b,1 1,12-tetrahydrobenzo [5,6-C] phenanthridine; Finally, nitidine chloride was obtained by aromatization, methylation of dimethyl sulfate and exchange of sodium chloride salt. The optimized process has a total yield of 2.5%, simple operation, mild reaction conditions, and economical and easy to obtain raw materials and reagents.
fig. 1 optimized synthesis route of nitidine chloride
at present, nitidine chloride is mainly extracted and separated from different Zanthoxylum plants, with a total yield of 0.003% ~ 0.07%. due to its poor water solubility, large-scale industrial extraction production has low efficiency and high cost. There are mainly four artificial synthesis methods: Arthur et al. use 3,4-dimethoxybenzaldehyde, 1-acetyl -3,4-methylene dioxybenzene as starting materials, and react with aldehydes and ketones to obtain 4.(benzo [d][1,3] dioxolane -5-base). 2-(3,4-dimethoxyphenyl) -4-oxobutyric acid (3); After reduction, Friedel reaction, Liu Carter reaction and cyclization, 2,3-methylenedioxy groups are obtained. 8,9-dimethoxy-4b,10b,11,12-tetrahydrobenzo [5,6.C] phenanthroline (7); Then aromatization and methylation of dimethyl sulfate were carried out by dry stirring reaction at 240 ℃ of 30% palladium carbon, and finally the final product 1E 53 was obtained by chlorination exchange with concentrated hydrochloric acid/zinc powder. Lv et al. use methyl 3,4-dimethoxy -5-iodobenzoate as the starting material, and are catalyzed by palladium dichloride [Pd(PPh3):C1:] and zinc powder for coupling cyclization reaction, and then methylation, aromatization of dichloride dicyano-benzoquinone, reduction of tetrahydrolithium aluminum, and finally acidification of hydrochloric acid to obtain 1.
effect nitidine chloride (Shanghai ronghe) mainly achieves anti-tumor effect through several mechanisms such as inhibiting topoisomerase activity, blocking cell cycle, inducing tumor cell apoptosis, reversing multidrug resistance of tumor cells, etc. As a new usage of traditional Chinese medicine, the anti-tumor effect of nitidine chloride has great development and application value [3].
reference materials [1] [journal papers] Guo guiyuan, Huang zicheng, Lin chan chan, Huang zhipeng-chinese journal of gerontology 2017 issue 9
[2] [journal papers] tan shanlun, zang chengxu, Dai Li, Huang jinghua, Zhang dazhi, TAN Shanlun, ZANG Chengxu, DAI Li, HUANG Jinghua, ZHANG Dazhi-china journal of pharmaceutical industry, issue 2, 2015
[3] nitidine chloride. 100-link database. [reference date 2017.08.23]
use used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: By inhibiting topoisomerase activity, blocking cell cycle, inducing tumor cell apoptosis, reversing tumor cell multidrug resistance and other mechanisms to achieve anti-tumor effects.
Last Update:2024-04-09 15:16:47
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