Dihydrolycorine

Base Information

• Chemical Name: Dihydrolycorine
• CAS No.: 6271-21-2
• Molecular Formula: C16H19NO4
• Molecular Weight: 289.329
• European Community (EC) Number: 683-122-2
• UNII: Z7N4S72301
• ChEMBL ID: CHEMBL583061
• DSSTox Substance ID: DTXSID701346488
• Nikkaji Number: J3.194.044C
• Mol file: 6271-21-2.mol

Synonyms:dihydrolycorine

Chemical Property of Dihydrolycorine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 247 °C
• Refractive Index: 1.701
• Boiling Point: 460.5 °C at 760 mmHg
• PKA: 14.13±0.40(Predicted)
• Flash Point: 232.3 °C
• PSA: 62.16000
• Density: 1.48 g/cm³
• LogP: 0.76640
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 289.13140809
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dihydrolycorine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC3=CC4=C(C=C3C5C2C1CC(C5O)O)OCO4
• Isomeric SMILES: C1CN2CC3=CC4=C(C=C3[C@H]5[C@H]2[C@H]1C[C@@H]([C@H]5O)O)OCO4
• Uses: Dihydrolycorine is a derivative of Lycorine, the main phenanthridine Amaryllidaceae alkaloid which exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli. Dihydrolycorine is a derivative of Lycorine (L487550), the main phenanthridine Amaryllidaceae alkaloid which exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli.
• Description: Dihydrolycorine is a derivative of the alkaloid lycorine that has antihypertensive and neuroprotective activities. It inhibits methoxamine-induced contraction of isolated rabbit aortic rings and rat anococcygeus muscle with pA2 values of 5.93 and 6.35, respectively. Dihydrolycorine reduces mean arterial pressure (MAP) in anesthetized and conscious normotensive rats when administered at a dose of 80 mg/kg. It also reduces electrically or phenylephrine-induced hypertension in pithed rats. Dihydrolycorine reduces infarct size, cerebral edema, and myeloperoxidase activity in a rat model of focal cerebral ischemia-reperfusion injury when administered following reperfusion.

Technology Process of Dihydrolycorine

There total 35 articles about Dihydrolycorine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

lycorine (476-28-8,6835-91-2,19312-40-4,66816-51-1) → dihydrolycorine (2030-55-9,6271-21-2,21851-15-0,30074-34-1,84236-20-4,89577-34-4,31387-87-8)

Guidance literature:

With hydrogen; platinum on activated charcoal; In acetic acid; under 1471.02 Torr; Ambient temperature;

DOI:10.1016/S0031-9422(00)80145-4

Reference yield:

→ dihydrolycorine (2030-55-9,6271-21-2,21851-15-0,30074-34-1,84236-20-4,89577-34-4,31387-87-8)

Guidance literature:

With palladium; acetic acid; Hydrogenation;

Reference yield:

(1S,2S,12bS,12cS)-1,2-diol-2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine hydrochloride (2188-68-3) → dihydrolycorine (2030-55-9,6271-21-2,21851-15-0,30074-34-1,84236-20-4,89577-34-4,31387-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium hydroxide / water / 16 h / 20 °C

2: acetic acid; palladium on activated charcoal; hydrogen / 20 h / 20 °C

With ammonium hydroxide; palladium on activated charcoal; hydrogen; acetic acid; In water;

DOI:10.1021/acs.orglett.8b02562

upstream raw materials:

(1α,2β)-1,2-dihydroxy-9,10-[methylenebis(oxy)]galanthan-7-one

lycorine

(1S,2S,12bS,12cS)-1,2-diol-2,4,5,7,12b,12c-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine hydrochloride

1α-acetoxy-9,10-methylenedioxy-12β-galanthan-2-one

Refernces

• 1、 Tasker, Sarah Z.,Cowfer, Amanda E.,Hergenrother, Paul J.. "Preparation of Structurally Diverse Compounds from the Natural Product Lycorine". supporting information. p. 5894 - 5898. Retrieved 2018/09/25.