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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O3
Molecular Weight 366.4534
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-HYDROXYETHYL (16.ALPHA.)-EBURNAMENINE-14-CARBOXYLATE

SMILES

[H][C@@]12N3CCC[C@@]1(CC)C=C(N4C5=C(C=CC=C5)C(CC3)=C24)C(=O)OCCO

InChI

InChIKey=WBEVCQPAHIHTRP-UNMCSNQZSA-N
InChI=1S/C22H26N2O3/c1-2-22-9-5-10-23-11-8-16-15-6-3-4-7-17(15)24(19(16)20(22)23)18(14-22)21(26)27-13-12-25/h3-4,6-7,14,20,25H,2,5,8-13H2,1H3/t20-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H26N2O3
Molecular Weight 366.4534
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 11:31:33 GMT 2023
Edited
by admin
on Sat Dec 16 11:31:33 GMT 2023
Record UNII
4LH862BJM2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-HYDROXYETHYL (16.ALPHA.)-EBURNAMENINE-14-CARBOXYLATE
Systematic Name English
RGH-10885
Code English
EBURNAMENINE-14-CARBOXYLIC ACID, 2-HYDROXYETHYL ESTER, (16.ALPHA.)-
Systematic Name English
RGH10885
Code English
(-)-TRANS-APOVINCAMINIC ACID 2-HYDROXYETHYL ESTER
Systematic Name English
Code System Code Type Description
FDA UNII
4LH862BJM2
Created by admin on Sat Dec 16 11:31:33 GMT 2023 , Edited by admin on Sat Dec 16 11:31:33 GMT 2023
PRIMARY
CAS
192813-34-6
Created by admin on Sat Dec 16 11:31:33 GMT 2023 , Edited by admin on Sat Dec 16 11:31:33 GMT 2023
PRIMARY
PUBCHEM
10474085
Created by admin on Sat Dec 16 11:31:33 GMT 2023 , Edited by admin on Sat Dec 16 11:31:33 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY
cmpd No.7b inhibition of diazepam-induced amnesia in (%): with 0.1 mg/kg p.o. = 74%, with 10.0 mg/kg p.o. = 65%; A series of trans-2'-hydroxyethyl and 2'-acyloxyethyl apovincaminates 4b- f and 7b- f has been synthesized and evaluated for their antioxidant and antiamnesic effects. The new esters were prepared from 4a and 7a ethyl esters or from the corresponding carboxylic acid sodium salt. For starting materials 11a, b, a new stereoselective trans-reduction was elaborated. From the combined results of the data obtained from in vitro and in vivo tests and examination of the metabolism, (3 R,16 S)-2'-hydroxyethyl apovincaminate ( 7b, RGH-10885) was identified as the most promising compound, owing to its potent neuroprotective and antiamnesic activities. The in vivo effectiveness of selected compounds on the cognitive functions was studied in a one-trial passive avoidance task and a water-labyrinth test.
ACTIVE MOIETY
From the combined results of the data obtained from in vitro and in vivo tests and metabolism studies, 2-hydroxyethyl (3R,16S)-apovincaminate (4b, RGH-10885) was identified as the most promising compound, owing to its potent neuroprotective and antiamnesic activities.7(see above)