68353-55-9

Basic information

• Product Name: 7-O-DeMethyl α-Narcotine
• Synonyms: 7-O-DeMethyl α-Narcotine
• CAS NO: 68353-55-9
• Molecular Formula: C₂₁H₂₁NO₇
• Molecular Weight: 399.39394
• Mol File: 68353-55-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 7-O-DeMethyl α-Narcotine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-DeMethyl α-Narcotine(68353-55-9)
• EPA Substance Registry System: 7-O-DeMethyl α-Narcotine(68353-55-9)

Safety Data

• Hazardous Substances Data: 68353-55-9(Hazardous Substances Data)

Usage

Description

7-O-DeMethyl α-Narcotine is a derivative of Narcotine, a noscapinoid class of microtubule binding compounds that alter microtubule dynamics without affecting tubulin polymer mass. It is a promising chemotherapeutic agent for the treatment of human cancers.
Used in Pharmaceutical Industry:
7-O-DeMethyl α-Narcotine is used as a chemotherapeutic agent for the treatment of human cancers. It shows great promise in this application due to its ability to alter microtubule dynamics without affecting tubulin polymer mass, making it a potential alternative to traditional chemotherapy drugs.
Used in Cancer Research:
7-O-DeMethyl α-Narcotine is used as a research tool for studying the effects of noscapinoids on microtubule dynamics and their potential as chemotherapeutic agents. This helps in understanding the mechanisms of action and identifying new targets for cancer treatment.
Used in Drug Development:
7-O-DeMethyl α-Narcotine is used in the development of new drugs for cancer treatment. Its unique properties as a microtubule binding compound make it a valuable candidate for the development of novel therapeutic agents with improved efficacy and reduced side effects compared to existing treatments.

Upstream product

• 68353-58-2 (S)-7-tert-butoxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one 
• 128-62-1 noscapine 
• 851983-58-9 5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl 
• 100-46-9 benzylamine 
• 3860-46-6 1R,9R-(-)-β-narcotine 

Downstream Products

• 128-62-1 noscapine 
• 870190-27-5 7-benzylamino-6-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one 
• 1314077-43-4 (S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzoate 
• 1314077-46-7 (S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzylcarbamate 

Relevant articles and documents

Novel third-generation water-soluble noscapine analogs as superior microtubule-interfering agents with enhanced antiproliferative activity

Noscapine, an opium-derived 'kinder-gentler' microtubule-modulating drug is in Phase I/II clinical trials for cancer chemotherapy. However, its limited water solubility encumbers its development into an oral anticancer drug with clinical promise. Here we report the synthesis of 9 third-generation, water-soluble noscapine analogs with negatively charged sulfonato and positively charged quaternary ammonium groups using noscapine, 9-bromonoscapine and 9-aminonoscapine as scaffolds. The predictive free energy of solvation was found to be lower for sulfonates (6a-c; 8a-c) compared to the quaternary ammonium-substituted counterparts, explaining their higher water solubility. In addition, sulfonates showed higher charge dispersability, which may effectively shield the hydrophobicity of isoquinoline nucleus as indicated by hydrophobicity mapping methods. These in silico data underscore efficient net charge balancing, which may explain higher water solubility and thus enhanced antiproliferative efficacy and improved bioavailability. We observed that 6b, 8b and 8c strongly inhibited tubulin polymerization and demonstrated significant antiproliferative activity against four cancer cell lines compared to noscapine. Molecular simulation and docking studies of tubulin-drug complexes revealed that the brominated compound with a four-carbon chain (4b, 6b, and 8b) showed optimal binding with tubulin heterodimers. Interestingly, 6b, 8b and 8c treated PC-3 cells resulted in preponderance of mitotic cells with multipolar spindle morphology, suggesting that they stall the cell cycle. Furthermore, in vivo pharmacokinetic evaluation of 6b, 8b and 8c revealed at least 1-2-fold improvement in their bioavailability compared to noscapine. To our knowledge, this is the first report to demonstrate novel water-soluble noscapine analogs that may pave the way for future pre-clinical drug development.

First noscapine glycoconjugates inspired by click chemistry

A number of novel 7-O-noscapine glycoconjugates have been synthesized starting from noscapine, an alkaloid found in the opium plant, via two successive steps. The first step is a selective 7-O-demethylation of noscapine and the next is a subsequent propar

Second generation benzofuranone ring substituted noscapine analogs: Synthesis and biological evaluation

Microtubules, composed of α/β tubulin heterodimers, represent a validated target for cancer chemotherapy. Thus, tubulin- and microtubule-binding antimitotic drugs such as taxanes and vincas are widely employed for the chemotherapeutic management of variou