75815-22-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-bromo-2'-chloropropiophenone is used as a reagent for the synthesis of 2-(tert-Butylamino)-3’,4’-dichloropropiophenone Hydrochloride (B690685). 2-bromo-2'-chloropropiophenone is an important intermediate in the production of various pharmaceuticals.
Used in the Synthesis of Bupropion (B689625, HCl):
2-bromo-2'-chloroprophenone is also an impurity in the synthesis of Bupropion (B689625, HCl), a medication with inhibitory effects on monoamine uptake. Bupropion is used to treat conditions such as depression and attention deficit hyperactivity disorder (ADHD). The presence of 2-bromo-2'-chloropropiophenone in the synthesis process highlights its importance in the development of this therapeutic agent.
Used in the Modulation of Nicotinic Acetylcholine Receptors (nAChRs):
Furthermore, 2-bromo-2'-chloropropiophenone plays a role in antagonizing the effects of human α3β4, α4β2, α4β4, and α1 nicotinic acetylcholine receptors (nAChRs). This makes it a valuable compound in the research and development of drugs targeting these receptors, which are involved in various neurological and cognitive functions.

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 609-65-4 o-chlorobenzoyl chloride 
• 22869-35-8 2-chloro-α-ethylbenzyl alcohol 
• 6323-18-8 2-chloropropiophenone 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 90919-30-5 1-o-Chlor-phenyl-1-methoxy-aceton 
• 90869-66-2 1-(2-chlorophenyl)-2-(methylamino)propan-1-one hydrochloride 

Relevant academic research and scientific papers

Structure-based design of potent human dihydroorotate dehydrogenase inhibitors as anticancer agents

It has been proven that inhibiting human dihydroorotate dehydrogenase (hDHODH) restricts the growth of rapidly proliferating cells, thus hDHODH can be developed as a promising target for the treatment of immunological disease and cancer. Here, a succession of substituted hydrazino-thiazole derivatives were designed, synthesized, and biologically evaluated through structure-based optimization, of which compound 22 was the most potent inhibitor of hDHODH with an IC50 value of 1.8 nM. Furthermore, 22 exhibited much better antiproliferative activity than brequinar, both in HCT-116 and BxPC-3 cancer cell lines. Flow cytometry analysis revealed that 22 induced S phase cell cycle arrest and promoted induction of apoptosis. All results established a proof that blocking the pyrimidine de novo synthesis pathway by inhibiting the rate-limiting enzyme hDHODH is an attractive therapy for cancer.

Diminished reactivity of ortho-substituted phenacyl bromides toward nucleophilic displacement

A systematic increase of substitution rates by tert-butylamine on α-bromopropiophenones is observed with meta or para substituents with increasing electron-withdrawing ability (k x 103 L M-1 min-1 = 12.7 (p-CH3), 15.7 (o-F), 20.5 (H), 20.0 (p-Cl), 23.6 (m-Cl), 27.3 (p-CF3)). Within an ortho-substituted series, the reactivities decrease (k x 103 L M-1 min-1 = 7.64 (o-OCH3), 5.31 (o-CH3), 2.85 (o-Cl), 2.40 (o-CF3)). Ortho-substitution results occur from rotational barrier effects and an Aδσ + Bδσ + repulsion. The major bonding contribution between reaction and α-substituent centers (A-B) is only the σ bond. When π bonding is allowed between A and B (meta/para-substitution), delocalization and stabilization of the reacting center occurs.

Pyrrole derivatives and medicinal composition

The invention relates to a pharmaceutical composition comprising a pyrrole derivative of the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate of either of them, as an active ingredient. STR1 (wherein R1 represents hydrogen or alkoxycar91 bonylamino, R2 represents alkyl, aryl which may be substituted, aromatic heterocyclyl which may be substituted, unsubstituted amino, monoalkylamino, dialkylamino, or cyclic amino which may be substituted; R3 represents cyano or carbamoyl; R4 represents hydrogen or alkyl; E represents alkylene; q is equal to 0 or 1, A represents methyl, aryl which may be substituted, or aromatic heterocyclyl which may be substituted). The pharmaceutical composition of the invention is effective for the treatment of pollakiuria or urinary incontinence.

Therapeutically useful 1-phenyl-2-piperidinoalkanol derivatives

Compounds of the formula: STR1 wherein R1 is hydrogen, halogen, trifluoromethyl, alkyl, hydroxyl, alkyoxy, benzyloxy, alkanoyloxy, or benzoyloxy, or when R2 is hydroxyl or methoxy in the 4-position and R3 is hydrogen, R1 may also represent hydroxymethyl carbamoyl or alkoxycarbonyl, R2 is hydrogen, halogen, alkyl, hydroxyl, or alkoxy, R3 is hydrogen or alkyl, R4 is alkyl (in which case the compounds are (±)-erythro) or when R3 represents hydrogen, R4 may also be hydrogen, and R5 is hydrogen, halogen, alkyl, alkoxy, or three methoxy groups in the 3-, 4- and 5-positions and pharmaceutically acceptable acid addition salts thereof, with the exclusion of compounds wherein: (a) one of R1 and R2 is in the 4-position and is hydroxyl, alkoxy or benzyloxy, the other is in the 3-position and is hydrogen, hydroxyl, alkoxy or benzyloxy, and R3 and R5 are hydrogen and wherein: (b) R1 is in the 4-position and is halogen, R4 is methyl and R2, R3 and R5 are hydrogen, are useful as medicaments.