Crinine
Descripción general
Descripción
Crinine is an alkaloid.
Aplicaciones Científicas De Investigación
Biological Activities of Crinine
This compound exhibits a remarkable range of biological effects, which have been documented through various studies:
- Antiviral Properties : this compound has shown promise in combating viral infections, although specific mechanisms remain to be fully elucidated .
- Antibacterial Effects : Research indicates that this compound possesses antibacterial activity, making it a candidate for developing new antimicrobial agents .
- Anti-cancer Potential : Studies have demonstrated that this compound can induce apoptosis in cancer cells, suggesting its role as a potential anti-cancer agent .
- Anti-malarial and Anti-plasmodial Activities : this compound has been evaluated for its effectiveness against malaria parasites, showing potential as a treatment option .
Synthesis of this compound
The synthesis of this compound-type alkaloids has been a focal point of research due to their complex structures and biological significance. Recent advancements in synthetic methodologies include:
- Enantioselective Synthesis : Bioinspired approaches utilizing iridium-catalyzed asymmetric hydrogenation have enabled the efficient synthesis of this compound-type alkaloids. This method allows for high yields and enantioselectivity .
- Synthetic Pathways : Various synthetic routes have been developed over the years, including the use of cyclohexenones and Claisen-type reactions to create key intermediates leading to this compound .
Clinical Applications
A notable clinical study compared the efficacy and tolerability of vaginal formulations containing this compound derivatives (e.g., Crinone 8% gel) for luteal support in in vitro fertilization (IVF) cycles. The findings indicated comparable pregnancy rates with improved tolerability for the this compound formulation .
Pharmacological Studies
A comprehensive review highlighted the pharmacological actions of this compound alongside other related alkaloids. It emphasized the need for further research to clarify the mechanisms underlying its biological activities and potential therapeutic uses .
Data Table: Summary of Biological Activities
Propiedades
Fórmula molecular |
C16H17NO3 |
|---|---|
Peso molecular |
271.31 g/mol |
Nombre IUPAC |
(1S,13R,15R)-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-15-ol |
InChI |
InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m0/s1 |
Clave InChI |
RPAORVSEYNOMBR-IUIKQTSFSA-N |
SMILES |
C1CN2CC3=CC4=C(C=C3C15C2CC(C=C5)O)OCO4 |
SMILES isomérico |
C1CN2CC3=CC4=C(C=C3[C@]15[C@H]2C[C@H](C=C5)O)OCO4 |
SMILES canónico |
C1CN2CC3=CC4=C(C=C3C15C2CC(C=C5)O)OCO4 |
Sinónimos |
crinine |
Origen del producto |
United States |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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