191864-24-1

Usage

Uses

Used in Pharmaceutical Industry:
Zolmitriptan Related Compound D (20 mg) ((S)-Ethyl 3-[2-(dimethylamino)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate) is used as a pharmaceutical compound for its agonistic action on the Serotonin 5HT1D-receptor. This makes it a potential candidate for the development of medications targeting conditions that involve the serotonin system, such as migraines and other headaches.
Used in Research and Development:
In the field of research and development, Zolmitriptan Related Compound D (20 mg) ((S)-Ethyl 3-[2-(dimethylamino)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate) can be utilized as a research tool to study the mechanisms of serotonin receptor agonists and their effects on various physiological processes. This can lead to a better understanding of the serotonin system and the development of new therapeutic strategies for related conditions.
Used in Drug Synthesis:
Zolmitriptan Related Compound D (20 mg) ((S)-Ethyl 3-[2-(dimethylamino)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate) may also be used in the synthesis of other related compounds with potential therapeutic applications. Its structural features can be modified to create new molecules with improved pharmacological properties or reduced side effects, contributing to the development of novel drugs for various medical conditions.

Upstream product

• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 5407-04-5 3-(dimethylamino)propyl chloride hydrochloride 
• 659738-68-8 (S)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-3-[(2-toluen-4-sulphonyloxy)ethyl]-1H-indol-2-carboxylic acid ethyl ester 
• 124-40-3 dimethyl amine 
• 50-00-0 formaldehyd 
• 868622-22-4 ethyl (S)-3-(2-aminoethyl)-5-((2-oxooxazolidin-4-yl)methyl)-1H-indole-2-carboxylate hydrochloride 
• 67-56-1 methanol 
• 868622-21-3 ethyl (S)-3-[2-(1,3-dioxoisoindolin-2-yl)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate 
• 139264-55-4 (S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one 
• 152305-23-2 (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one 
• 17193-40-7 (S)-4-nitrophenylalanine methyl ester hydrochloride 
• 89288-22-2 (S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol 
• 69472-61-3 2-acetyl-5-dimethylaminopentanoic acid ethyl ester 
• 63-91-2 L-phenylalanine 

Downstream Products

• 139264-17-8 zolmitriptan 

Relevant academic research and scientific papers

Synthesis of zolmitriptan and related substances

Efficient and cost-effective synthesis of Zolmitriptan 1 employing Japp-Klingemann reaction and a new robust purification strategy is described.

Process for preparing optically pure zolmitriptan

A process for preparing zolmitriptan, proceeding through the intermediate Ethyl-3-[2-(1,3-dioxo-2,3-dihydro-1H-2-isoindoleyl)ethyl]-5-[(4S)-2-oxo-1,3-oxazolan-4-ylmethyl]-1H-2-indole carboxylate.

PROCESS FOR PREPARING ZOLMITRIPTAN COMPOUNDS

In particular, zolmitriptan or a pharmaceutically acceptable salt thereof, which includes a) Preparation of the diazonium salt of the aniline hydrochloride (II); followed by reduction and acidification to give hydrazine (III); b) In situ Reaction of the hydrazine hydrochloride (III) with ?-keto-?-valerolactone, to give the hydrazone (IV); c) Fischer indole synthesis of the hydrazone (IV), to give the pyranoindolone of formula (V); d) Transesterification of the pyranoindolone (V) to provide the compound (VI), in which R means a straight or branched C1-C4 alkyl; e) Conversion of the hydroxyl group of the compound (VI) into dimethylamino to give the indolecarboxylate (VII), in which R means a straight or branched C1-C4 alkyl; f) Saponification of the 2-carboalkoxy group of the compound (VII), to provide indolecarboxylic acid (VIII); g) Decarboxylation of the indolecarboxylic acid (VIII), to provide zolmitriptan and, eventually, to provide a pharmaceutically acceptable salt thereof.

A novel series of 2,5-substituted tryptamine derivatives as vascular 5HT(1B/1D) receptor antagonists

The design, synthesis, and activity of a novel series of 2,5- substituted tryptamine derivatives at vascular 5HT(1B)-like receptors is described. Several important auxiliary binding sites of the 5HT(1B)-like receptor have been proposed following various modifications to the 2- substituent and especially to the methylene- or ethylene-linked 5-side chain. Careful design of new molecules based on a proposed pharmacophoric model of the 5HT(1B)-like receptor has resulted in the discovery of ethyl 3-[2- (dimethylamino)ethyl]-5-[2-(2,5-dioxo-1-imidazolidinyl)ethyl]-1H-indole-2- carboxylate (40), a highly potent, silent, competitive, and selective antagonist which shows affinity at the vascular 5HT(1B)-like receptors only. Changes to the size of the 2-ester substituent have a significant effect on affinity at the 5HT(1B)-like receptor and other receptors. Prudent placement of the carbonyl substituent in the heterocycle of the 5-side chain is crucial for good affinity and selectivity over the 5HT(2A) and other receptors. Several key structural and electronic features were identified which are crucial for producing antagonism within a tryptamine-based series. An electron deficient indole ring system appears essential in order to achieve antagonism, and this is achieved by the inclusion of electron-withdrawing groups at the 2-position of the indole ring. The molecule displacement within the receptor resulting from the inclusion of the bulky 2-substituents also enhances antagonism as this results in the removal of the Π electon density of the indole ring from the region of the receptor normally occupied by the indole ring of 5HT. There also appears to be a structural requirement on the side chain incorporating the protonatable nitrogen, and this is achieved by the inclusion of the bulky 2-ester group which neighbors the 3-ethylamine side chain.