09-26-00 15:35
No 54985
OK,
I realize this isn't a typical chemical synthesize, but I was wondering if anyone could help me out.
I would like to try synthesizing zolmiptriptan. I had considered a couple of different methods and basically couldn't figure out how to put them together wihtout destroying the initial reactants.
http://www.eskimo.com/~robertc/synthesis
So.....
Do any of you chemists have some ideas to help? Or does anyone know where the best place to get the patented synthesis process would be.
Thanks in advance.
(Chief Bee)
09-27-00 13:26
No 55142
Look up its synthesis in the Merck Index or something. Fusing that lactam with your indole isn't gonna happen.
http://rhodium.lycaeum.org
(Hive Bee)
09-29-00 03:21
No 55602
Zolmitriptan ? why?
(Newbee)
09-29-00 04:12
No 55621
Actually I might be able to find something on this. Zomig is a odd molecule in that it has a dmt counterpart and also a amphetamine counterpart.Here are some references I found on beilstein.
Substance
Registry Number 7415009Name zolmitriptan 4-[3-(2-
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Pharmacological Data 1 of 3
1 contraction of the New Zealand white rabbit saphenous vein, pD&2%: 6.1; maximum contraction relative to 5-HT, 1.48. 1 6048434; Journal; Perez, M.; Ayerbe, N.; Fourrier, C.; Sigogneau, I.; Pauwels, P. J.; et al.; EJMCA5; Eur.J.Med.Chem.Chim.Ther.; EN; 32; 2; 1997; 129-134;
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Pharmacological Data 2 of 3
1 binding affinities at cloned human receptors, K&i% (nM): 5-HT&1D$a% - 0.92, 5-HT&1D$b% - 4.2, 5-HT&1A% - 78.6; inhibition of forskolin-induced cAMP formation in a stably transfected CHO-K1 cell line, EC50: 15.7 nM. 1 6048434; Journal; Perez, M.; Ayerbe, N.; Fourrier, C.; Sigogneau, I.; Pauwels, P. J.; et al.; EJMCA5; Eur.J.Med.Chem.Chim.Ther.; EN; 32; 2; 1997; 129-134;
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Pharmacological Data 3 of 3
1 binding affinities at cloned human 5-HT&1D$a%, 5-HT&1D$b% (EC50=15 nM) and 5-HT&1A% receptors; functional activity: contraction of the New Zealand white rabbit saphenous vein. 1 6001415; Journal; Perez, Michel; Fourrier, Catherine; Sigogneau, Isabelle; Pauwels, Petrus J.; Palmier, Christiane; et al.; JMCMAR; J.Med.Chem.; EN; 38; 18; 1995; 3602-3607;
Reaction
ID 4337486BRN 1209228 formaldehyde 7414433 (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-
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Reaction Details
Classification Preparation 31 percent (BRN=7415010) NaCNBH3, glacial AcOH methanolConditions Ambient temperature. 1 6001396; Journal; Glen, Robert C.; Martin, Graeme R.; Hill, Alan P.; Hyde, Richard M.; Woollard, Patrick M.; et al.; JMCMAR; J.Med.Chem.; EN; 38; 18; 1995; 3566-3580;
Citation Number
Number 6001396
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Citation
Type Journal Glen, Robert C.; Martin, Graeme R.; Hill, Alan P.; Hyde, Richard M.; Woollard, Patrick M.; et al. JMCMARTitle J.Med.Chem.Code EN(Serie
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Abstract
Computer-Aided Design and Synthesis of 5-Substituted Tryptamines and Their Pharmacology at the 5-HT&1D% Receptor: Discovery of Compounds with Potential Anti-Migraine Properties The design and synthesis of a series of novel 5-substituted tryptamines with pharmacological activity at 5-HT&1D% and other monoamine receptors is described.Structural modifications of N- and C-linked (prinicipally hydantoin) analogues at the 5-position were synthesized and their pharmacological activities were utilized to deduce significant steric and electrostatic requirements of the 5-HT&1D% and 5-HT&2A% receptor subtypes.Conformations of the active molecules were computed which, when overlaid, suggested a pharmacophore hypothesis which was consistent with the affinity and selectivity measured at 5-HT&1D% and 5-HT&2A% receptors.This pharmacophore is composed of a protonated amine site, an aromatic site, a hydrophobic pocket, and two hydrogen-bonding sites.A 'selectively site' was also identified which, if occupied, induced selectivity for 5-HT&1D% over 5-HT&2A% in this series of molecules.The development and use of the pharmacophore models in compound design is described.In addition, the physicochemical constraints of molecular size and hydrophobicity required for efficient oral absorption are discussed.Utilizing the pharmacophore model in conjuction with the physicochemical constraints of molecular size and log D&pH7.4% led to the discovery of 311C90 (6), a new selective 5-HT&1D% agonist with good oral absorption and potential use in the treatment of migraine. EN
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Substance 1 of 158
Registry Number 110598Preferred RN 461-72-3Registry Number 461-72-3Name imidazolidine-2,4-di
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Substance 2 of 158
Registry Number 125513Preferred RN 61-54-1Registry Number 61-54-1Name 2-indol-3-yl-ethylami
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Substance 3 of 158
Registry Number 134111Preferred RN 1821-47-2Registry Number 1821-47-2Name 2-(5-methyl-indol-3
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Substance 4 of 158
Registry Number 160628Preferred RN 487-93-4Registry Number 487-93-4Name 3-(2-dimethylamino-e
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Substance 5 of 158
Registry Number 237397Registry Number 68319-44-8, 103273-88-7, 123944-77-4Name 5-(4-nitro-benzyl)-imida
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