Isocorydine

Base Information

• Chemical Name: Isocorydine
• CAS No.: 475-67-2
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• UNII: 3B5E87JEOX
• DSSTox Substance ID: DTXSID201023580
• Nikkaji Number: J5.971D
• Wikidata: Q27106973
• Metabolomics Workbench ID: 44240
• ChEMBL ID: CHEMBL489525
• Mol file: 475-67-2.mol

Synonyms:isocorydine;isocorydine hydrochloride, (S)-isomer;isocorydine, (R)-isomer;isocorydine, (S)-isomer

Chemical Property of Isocorydine

Chemical Property:

• Vapor Pressure: 7.29E-11mmHg at 25°C
• Melting Point: 216-220 °C(lit.)
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 506.1°Cat760mmHg
• PKA: 9.41±0.20(Predicted)
• Flash Point: 259.9°C
• PSA: 51.16000
• Density: 1.222g/cm³
• LogP: 3.10800
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Isocorydine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)OC)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC)OC
• Description: Isocorydine is an aporphine alkaloid that has been found in A. squamosa that has vasodilatory and anticancer activities. It reduces the action potential duration and increases the effective refractory period in isolated canine Purkinje fibers when used at a concentration of 30 μM. Isocorydine induces relaxation of norepinephrine-precontracted isolated rabbit aortic strips with an EC50 value of 12.6 μM. It is cytotoxic to A549 lung cancer cells (IC50 = 197.7 μM), as well as Huh7, HepG2, SNU-449, and SNU-387 hepatic cancer cells (IC50s = 161.3, 148, 262.2, and 254.1 μg/ml, respectively). Isocorydine, in combination with doxorubicin, reduces tumor growth in a Huh7 mouse xenograft model.
• Uses: sedative, cholinergic Isocorydine is an alkaloid inhibitor of eukaryotic kinases.

Technology Process of Isocorydine

There total 7 articles about Isocorydine 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: 86.0%

(S)-11-benzyloxy-5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinoline → isocorydine (475-67-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 6h; under 2250.23 Torr;

DOI:10.1016/j.tetasy.2015.09.008

Reference yield: 11.0%

methanol (67-56-1) + C19H21NO4 → C20H25NO5 + isocorydine (475-67-2)

Guidance literature:

With methanesulfonic acid; at 80 - 110 ℃; for 0.25h;

DOI:10.1021/acs.orglett.6b02333

Reference yield:

C26H30N2O6S → C20H25NO5 + isocorydine (475-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1,4-dioxane / 8 h

2: methanesulfonic acid / 0.25 h / 80 - 110 °C

With methanesulfonic acid; sodium hydroxide; In 1,4-dioxane;

DOI:10.1021/acs.orglett.6b02333

upstream raw materials:

formaldehyd

(6aS)-(+)-norisocorydine

methanol

(Z,E)-sinomenine oxime

Downstream raw materials:

O,O-Dimethylcorytuberin

isocorydine hydrochloride

menisperine iodide

corytuberine

Refernces

A BIOMIMETIC SYNTHESIS OF <+/->-CORYNOLINE, <+/->-11-EPICORYNOLINE, <+/->-ISOCORYNOLINE, AND <+/->-EPIISOCORYNOLINE FROM CORYSAMINE

10.1016/S0040-4039(00)82413-2

The research focuses on the biomimetic synthesis of hexahydrobenzo[c]phenanthridine alkaloids, specifically (+)-corynoline, (+)-ll-epicorynoline, (+)-isocorynoline, and (+)-ll-epiisocorynoline, from the protoberberine alkaloid corysamine. The purpose of this study was to develop a novel and efficient synthetic route that mimics the biogenetic process, providing a general method for the synthesis of these alkaloids. The researchers achieved this by transforming corysamine into the target alkaloids through a series of chemical reactions involving enamine-aldehyde (3) as a proposed biogenetic intermediate. Key chemicals used in the process included thallium (III) nitrate for oxygenation, sodium borohydride, hydrochloric acid, and sodium cyanoborohydride for reduction and cyclization, as well as lithium aluminum hydride and sodium cyanoborohydride for further reduction steps. The conclusions of the study were that the developed synthetic method was not only biomimetic but also simple and efficient, offering a practical approach to synthesizing hexahydrobenzo[c]phenanthridine alkaloids.