313692-52-3

Upstream product

• 21086-33-9 2-bromo-1-(4-methoxyphenyl)-1-propanone 
• 121-97-1 4-Methoxypropiophenone 

Downstream Products

• 80096-48-6 (+/-)-4-Methoxycathinone 
• 124235-34-3 2,5-bis-methyl-3,6-bis-(4'-methoxyphenyl)-pyrazine 
• 308143-11-5 2-amino-3-cyano-4-(4-methoxyphenyl)-5-methylpyrrole 
• 42416-75-1 4'-methoxy-2-aminopropiophenone hydrochloride 
• 1595999-21-5 2-azido-1-(4-methoxyphenyl)propan-1-ol 

Relevant academic research and scientific papers

Catalytic Lewis and Br?nsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes

A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.

Kinetic diastereomer differentiation in Au(III)- and Bi(III)-catalyzed benzylic arylation: Concise and stereocontrolled synthesis of 2-amino-1,1-diarylalkanes

Benzylic alcohols carrying an adjacent α-nitro or α-azido group on the alkane chain are converted into syn-1,1-diaryl-2-nitro- and 2-azidoalkanes with electron-rich arenes in stereoselective reactions catalyzed by Bronsted and Lewis acids. Gold(III) chloride and bismuth(III) triflate were found to be especially efficient as catalysts, showing kinetically controlled differentiation in the reactivity of diastereomeric α-substituted benzyl alcohols. Applications to therapeutically relevant syn- and anti- 2-amino-1,1-diarylalkanes are projected.

Estrogenic diazenes: Heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes

Estrogens regulate many biological functions, often acting in a tissue-selective manner. Their tissue-selective action is believed to involve differential estrogen action through the two estrogen receptor (ER) subtypes, ERα and ERβ, as well as differential interaction of the ligand-receptor complexes with promoters and coregulator proteins. In the latter case, selectivity is based on the induction of specific conformations of the ligand-ER complex, conformations that are influenced by the structure of the ligand. Estrogen pharmaceuticals having an ideal balance of tissue-selective activity are being sought for menopausal hormone replacement, breast cancer prevention and therapy, and other actions. To expand on the structural diversity of ER ligands that might show such tissue selectivity, we have prepared a series of diazenes (pyrazines, pyrimidines, and pyridazines) substituted with two to four aryl groups and various short-chain aliphatic substituents. All of the pyrazine and pyrimidines bind to ER, some with high affinity and with a considerable degree of preferential binding to either ERα or ERβ. One pyrimidine and one pyrazine have ERα affinity preferences as high as 23 and 9, respectively, and one pyrimidine has an ERβ affinity preference of 8. The pyridazines, by contrast, are quite polar and have only very low binding affinity for the ER. In cell-based transcription assays, several of the pyrimidines and a pyrazine were found to be considerably more agonistic on ERα than on ERβ. Because these triaryl diazenes have the largest volumes among the ER ligands so far investigated, their high affinity demonstrates the flexibility of the ligand binding pocket of the ERs and its tolerance for large substituents. Thus, these novel heterocyclic ligands expand the repertoire of chemical structures that bind to the estrogen receptor, and they could prove to be useful in elucidating the biological behavior of the two ER subtypes and in forming the basis for new estrogen pharmaceuticals having desirable tissue selectivity.

Initial structure-activity relationship studies of a novel series of pyrrolo[1,2-a]pyrimid-7-ones as GnRH receptor antagonists

Initial SAR studies on 1-aminomethyl-2-aryl-3-cyano-pyrrolo[1,2-a]pyrimid-7-one-6-carboxylates as human GnRH receptor antagonists were discussed. 2-(2-Methylaminoethyl)pyridine was discovered to be a key feature for generating active compounds. The best compound from the series had 25 nM (Ki) binding affinity to human GnRH receptor.

Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein Ar, B, R1, R2, R3a, R3b, R4, R5, R6and m are as defined herein.

An effective synthesis of α-azido ketones from ketones

One-pot transformation of ketones into α-azido ketones has been achieved by successive treatment with HNIB and NaN3 in acetonitrile.