1205-36-3

Usage

Physical state

Yellow crystalline solid

Uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Functional groups

Ketone, bromine, nitro group

Importance

Building block for the production of various organic compounds, used in chemical research and as a starting material for the synthesis of complex organic molecules with bioactive and pharmacological properties

Potential applications

Antiviral and antifungal agent in the pharmaceutical industry

Upstream product

• 17408-16-1 3'-nitropropiophenone 

Downstream Products

• 135696-55-8 2-[1-Methyl-2-(3-nitro-phenyl)-2-oxo-ethyl]-isoindole-1,3-dione 
• 40035-46-9 2-(3-Nitrobenzoyl)propanenitrile 
• 16942-64-6 2-amino-5-methyl-4-(3-nitrophenyl)thiazole 
• 42075-28-5 3-m-nitrobenzoyl butyric acid 
• 36725-30-1 5-methyl-6-(3-nitrophenyl)-4,5-dihydro-2H-pyridazin-3-one 
• 36725-31-2 6-(3-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one 
• 172848-53-2 2-bromoacetylamino-5-methyl-4-(3-nitrophenyl)thiazole 
• 154922-48-2 6-methoxy-2-methyl-3-(3-nitrophenyl)benzofuran 
• 40217-29-6 3,6-dimethyl-4-(3-nitro-phenyl)-1H-pyridin-2-one 
• 40035-61-8 3,5,6-Trimethyl-4-(3-nitro-phenyl)-1H-pyridin-2-one 
• 40035-47-0 2-Chloro-3,6-dimethyl-4-(3-nitro-phenyl)-pyridine 
• 40035-62-9 2-Chloro-3,5,6-trimethyl-4-(3-nitro-phenyl)-pyridine 
• 40035-48-1 4-(3-Aminophenyl)-2,5-dimethylpyridine 
• 40035-63-0 4-(3-Aminophenyl)-2,3,5-trimethylpyridine 

Relevant academic research and scientific papers

2-AMINOIMIDAZOLE-PHENYL DERIVATIVES USEFUL FOR CONTROLLING MICROBIAL GROWTH

Provided are 2-aminoimidazole-phenyl derivative compounds of Formula (I): which compounds are useful in methods of controlling microbial growth, such as by enhancing the effects of an antibiotic administered in combination with the compound. Compositions

Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for smoking cessation

Bupropion (2a) analogues were synthesized and tested for their ability to inhibit monoamine uptake and to antagonize the effects of human α3β4*, α4β2, α4β4, and α1 * nAChRs. The analogues were evaluated for their ability to block nicotine-induced effects in four tests in mice. Nine analogues showed increased monoamine uptake inhibition. Similar to 2a, all but one analogue show inhibition of nAChR function selective for human α3β4*-nAChR. Nine analogues have higher affinity at α3β4*-nAChRs than 2a. Four analogues also had higher affinity for α4β2 nAChR. Analogues 2r, 2m, and 2n with AD50 values of 0.014,0.015, and 0.028 mg/kg were 87,81, and 43 times more potent than 2a in blocking nicotine-induced antinociception in the tail-flick test. Analogue 2x with IC50 values of 31 and 180 nM for DA and NE, respectively, and with IC50 of 0.62 and 9.8 μm for antagonism of α3β4 and α4β2 nAChRs had the best overall in vitro profile relative to 2a.

Potent s-cis-locked bithiazole correctors of ΔF508 cystic fibrosis transmembrane conductance regulator cellular processing for cystic fibrosis therapy

N-(5-(2-(5-Chloro-2-methoxyphenylamino)thiazol-4-yl)-4-methylthiazol-2-yl) pivalamide 1 (compound 15Jf) was found previously to correct defective cellular processing of the cystic fibrosis protein ΔF508-CFTR. Eight C4′-C5 C,C-bond-controlling bithiazole analogues of 1 were designed, synthesized, and evaluated to establish that constraining rotation about the bithiazole-tethering has a significant effect on corrector activity. For example, constraining the C4′-C5 bithiazole tether in the s-cis conformation [N-(2-(5-chloro-2- methoxyphenylamino)-7,8-dihydro-6H-cyclohepta[1,2-d:3,4-d′] bithiazole-2′-yl)pivalamide, 29] results in improved corrector activity. Heteroatom placement in the bithaizole core is also critical as evidenced by the decisive loss of corrector activity with s-cis constrained N-(2-(5-chloro-2- methoxyphenylamino)-5,6-dihydro-4H-cyclohepta[1,2-d:3,4-d′] bithiazole-2′-yl)pivalamide 33. In addition, computational models were utilized to examine the conformational preferences for select model systems. Following our analysis, the "s-cis-locked" cycloheptathiazolothiazole 29 was found to be the most potent bithiazole corrector, with an IC50 of ～450 nM.

Synthesis and structure-activity relationships of cis-tetrahydrophthalazinone/pyridazinone hybrids: A novel series of potent dual PDE3/PDE4 inhibitory agents

In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,-8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC50 = 7.0-8.7), whereas the pIC50 values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30μmol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.

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.

Studies on Cerebral Protective Agents. VIII. Synthesis of 2-Aminothiazoles and 2-Thiazolecarboxamides with Anti-anoxic Activity

Various 2-aminothiazoles (2a-s and 3a-g) and 2-thiazolecarboxamides (4a-h), possessing a nitrogeneous basic moiety at the C-2 position of the thiazole ring, were prepared and tested for anti-anoxic (AA) activity in mice.Among them, N-4-(3-trifluoromethylphenyl)-2-thiazolecarbaxamide hydrochloride (4e, FR108143) (minimum effective doses of 3,2 mg/kg i.p. and 10 mg/kg p.o., respectively) exhibited more potent AA activity than either FK360 or compound 1, each of which has a nitrogeneous basic moiety at the C-5 position.The structure-activity relationship with regard to AA activity of this series of compounds are discussed, and the three-dimensional electrostatic potentials (3D-MEP) around the basic nitrogen atom of FK360 and the thiazole derivative (4e) are compared.Key words cerebral protective agent; anti-anoxia; 2-aminothiazole; 2-thiazolecarboxamide; structure-activity relationship; FK360