Nitidine chloride
Nitidine chloride
CAS: 13063-04-2
Molecular Formula: C21H18NO4+
Nitidine chloride - 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 |
Nitidine chloride - Physico-chemical Properties
| Molecular Formula | C21H18NO4+ |
| Molar Mass | 348.37 |
| Density | 1.35g/cm3 |
| Melting Point | 283-286 °C |
| Boling Point | 619°C at 760 mmHg |
| Flash Point | 189.4°C |
| Solubility | Soluble in DMSO |
| Vapor Presure | 3.01E-15mmHg at 25°C |
| Appearance | Pale yellow needle crystal (methanol) |
| Color | white to beige |
| Storage Condition | -20°C |
| Refractive Index | 1.696 |
| MDL | MFCD01659688 |
| Physical and Chemical Properties | It is derived from Zanthoxylum nitidum. |
Nitidine chloride - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | DF4935500 |
| HS Code | 29399990 |
Nitidine chloride - 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 |
Nitidine chloride - 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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