115219-10-8

Basic information

• Product Name: 2-Bromo-6-methyl-8β-[(2-phenyl-1H-imidazol-1-yl)methyl]ergoline
• Synonyms: 2-Bromo-6-methyl-8β-[(2-phenyl-1H-imidazol-1-yl)methyl]ergoline;BAM-1303
• CAS NO: 115219-10-8
• Molecular Formula: C25H25 Br N4
• Molecular Weight: 461.3968
• Mol File: 115219-10-8.mol

Chemical Properties

• Boiling Point: 658.2°Cat760mmHg
• Flash Point: 351.9°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 3.37E-17mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: 2-Bromo-6-methyl-8β-[(2-phenyl-1H-imidazol-1-yl)methyl]ergoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-methyl-8β-[(2-phenyl-1H-imidazol-1-yl)methyl]ergoline(115219-10-8)
• EPA Substance Registry System: 2-Bromo-6-methyl-8β-[(2-phenyl-1H-imidazol-1-yl)methyl]ergoline(115219-10-8)

Safety Data

• Hazardous Substances Data: 115219-10-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C25H25BrN4/c1-29-14-16(15-30-11-10-27-25(30)17-6-3-2-4-7-17)12-19-18-8-5-9-21-23(18)20(13-22(19)29)24(26)28-21/h2-11,16,19,22,28H,12-15H2,1H3/t16?,19-,22-/m1/s1

Upstream product

• 670-96-2 2-Phenylimidazole 
• 74627-26-2 Toluene-4-sulfonic acid (6aR,9R,10aR)-5-bromo-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester 
• 68299-81-0 2-bromo-6-methyl-ergoline-8β-carboxylic acid methyl ester 
• 160730-40-5 (5R,8R,10R)-2-bromo-6-methyl-8-ergolinemethanol 
• 5878-43-3 9,10-dihydrolysergic acid 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 162070-43-1 (5R,8S,10R)-2-bromo-6-methyl-8-ergolinylmethyl p-toluenesulfonate 
• 115178-34-2 (6aR,9S,10aR)-7-Methyl-9-(2-phenyl-imidazol-1-ylmethyl)-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 

Relevant articles and documents

Synthesis and structure-activity relationships of new (5R,8S,10R)-ergoline derivatives with antihypertensive of dopaminergic activity

A series of new (5R,8S,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were evaluated in conscious spontaneously hypertensive rats and in rats with unilateral 6-hydroxydopamine-induced lesions of the substantia nigra, respectively. (5R,8S,10R)-6-Methyl-8-ergolinemethanols, prepared from the corresponding ergolinecarboxylates, were converted to the tosylates, which were treated with various five-membered heterocycles containing nitrogen atoms to afford the new ergolines. (5R,8S,10R)-8-(1-Imidazolylmethyl)-6-methylergoline (5a, BAM-2101) and (5R,8S,10R)-2-bromo-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline (7c, BAM-2202) exhibited potent antihypertensive activities. The maximum falls of systolic blood presure after oral administration of 5a and 7c at 3 mg/kg were 95 and 132 mmHg, respectively, while those of cianergoline, bromocriptine mesylate, hydralazine, and nifedipine at the same dose were 40, 37, 47, and 49 mmHg, respectively. The durations of significant antihypertensive effects of these compounds except nifedipine were more than 7 h. None of the ergolines exhibited potent dopaminergic activity. Structure-activity relationships are discussed.

Synthesis and structure-activity relationships of new (5R,8R,10R)-ergoline derivatives with antihypertensive or dopaminergic activity

A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6- hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6- Alkyl-8-ergolinemethanols, prepared from the corresponding ergolinecarboxylates, were converted to the tosylates, which were treated with various five-membered heterocycles containing nitrogen atoms to afford the new ergolines. (5R,8R,10R)-8-(1,2,4-Triazol-1-ylmethyl)-6-methylergoline (4s, maleate: BAM-1110) exhibited potent dopaminergic activity, about 18- fold greater than that of bromocriptine mesylate. (5R,8R,10R)-8-(1,2,4- Triazol-1-ylmethyl)-6-propylergoline (8b, fumarate: BAM-1602) showed extremely potent dopaminergic activity, being about 220 and 1.15 times more active than bromocriptine mesylate and pergolide mesylate, respectively. Several compounds exhibited potent antihypertensive activity. Structure- activity relationships for antihypertensive and dopaminergic activities are discussed.