6358-06-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5-aminophenol is used as an intermediate in the synthesis of various pharmaceutical compounds for its versatile chemical properties.
Used in Antimalarial Drug Synthesis:
2-Chloro-5-aminophenol is used as a key intermediate in the synthesis of antimalarial quinolones. These quinolones are effective against malaria, a widespread and life-threatening disease, particularly in tropical and subtropical regions.
Used in Anti-HIV Agent Synthesis:
2-Chloro-5-aminophenol is also utilized in the synthesis of potent anti-HIV agents based on pyrimidinylphenylamine 1. These agents are crucial in the development of treatments for HIV/AIDS, a global health concern.

InChI:InChI=1/C6H6ClNO/c7-5-2-1-4(8)3-6(5)9/h1-3,9H,8H2

Upstream product

• 619-10-3 5-nitro-2-chlorophenol 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 13726-14-2 4-chloro-m-anisidine 
• 121-88-0 5-Nitro-2-aminophenol 

Downstream Products

• 28443-47-2 (4-chloro-3-hydroxy-phenyl)-urea 
• 55302-68-6 C₁₆H₁₈ClN₃O₃ 
• 69342-26-3 N-(4-chloro-3-hydroxyphenyl)-N',N'-dimethylurea 
• 876314-61-3 2-chloro-5-(thiazol-2-ylamino)phenol 
• 933045-91-1 2-chloro-5-(pyridin-2-ylamino)phenol 
• 933046-00-5 2-chloro-5-(4-methylpyrimidin-2-ylamino)phenol 
• 915774-30-0 2-chloro-5-((4-methoxypyrimidin-2-yl)amino)phenol 
• 876314-63-5 2-chloro-5-(4-hydroxymethyl-pyrimidin-2-ylamino)-phenol 
• 918340-61-1 2-chloro-5-(pyrrolo[1,2-c]pyrimidin-1-ylamino)-phenol 
• 918340-62-2 2-chloro-5-(pyrrolo[1,2-a]pyrazin-1-ylamino)-phenol 
• 918340-57-5 2-chloro-5-(furo[2,3-d]pyrimidin-4-ylamino)-phenol 
• 345893-27-8 tert-butyl (4-chloro-3-hydroxyphenyl)carbamate 
• 345892-62-8 N-[4-Iodo-3-(2-dimethylamino-ethoxy)-phenyl]-3,4-dimethoxy-benzenesulfonamide 
• 119004-90-9 N-(4-chloro-3-hydroxy)phenyl-2',2',2'-trifluoroacetamide 

Relevant academic research and scientific papers

Novel Series of Dihydropyridinone P2X7 Receptor Antagonists

Identification of singleton P2X7 inhibitor 1 from HTS gave a pharmacophore that eventually turned into potential clinical candidates 17 and 19. During development, a number of issues were successfully addressed, such as metabolic stability, plasma stability, GSH adduct formation, and aniline mutagenicity. Thus, careful modification of the molecule, such as conversion of the 1,4-dihydropyridinone to the 1,2-dihydropyridinone system, proper substitution at C-5″, and in some cases addition of fluorine atoms to the aniline ring allowed for the identification of a novel class of potent P2X7 inhibitors suitable for evaluating the role of P2X7 in inflammatory, immune, neurologic, or musculoskeletal disorders.

Design, synthesis and biological evaluation of 3-benzyloxy-linked pyrimidinylphenylamine derivatives as potent HIV-1 NNRTIs

A novel series of 3-benzyloxy-linked pyrimidinylphenylamine derivatives (8a-8s) was designed, synthesized and evaluated for their in vitro anti-HIV activity in MT-4 cell cultures. Most of the compounds inhibited wild-type (wt) HIV-1 replication in the lower micromolar concentration range (EC50 = 0.05-35 μM) with high selectivity index (SI) values (ranged from 10 to >4870). In particular, 8h and 8g displayed excellent antiretroviral activity against wt HIV-1 with low cytotoxicity (EC50 = 0.07 μM, CC 50 >347 μM, SI >4870; EC50 = 0.05 μM, CC 50 = 42 μM, SI = 777, respectively), comparable to that of the marked drug nevirapine (EC50 = 0.113 μM, CC50 >15 μM, SI >133). In order to confirm the binding target, 8h was selected to perform the anti-HIV-1 RT assay. Additionally, preliminary structure activity relationship (SAR) analysis and molecular docking studies of newly synthesized compounds were also discussed, as well as the predicted physicochemical properties.

DIHYDROPYRIMIDONE AMIDES AS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R1, R2, R3, R4, R5, Ra and Rb are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

FUSED TRIAZOLE AMINES AS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein X, Y, R1, R2, and R3 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of dise

DIHYDROPYRIDONE UREAS AS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R1, R2, R3, R4 and R5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

DIHYDROPYRIDONE AMIDESAS P2X7 MODULATORS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, n, R1, R2, R3, R4, R5 and Ra are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor.

COMPOUNDS AND METHODS FOR THE TREATMENT OF VIRUSES AND CANCER

The present invention relates to compounds according to the formula I: Where Ra is H or an optionally OH-substituted C1-C3 alkyl; R1 is OR1, an optionally substituted C4-12 carbocyclic group which may be saturated or unsaturated (including aromatic) or an optionally substituted heterocyclic group; R1 is an optionally substituted C1-C14 hydrocarbyl group or an optionally substituted heterocyclic group;; R2 , R3 and R4 are each independently H, an optionally substituted C1-C4 alkyl group (preferably CH3, CH2CH3 or CF3), halogen (preferably F, Cl, Br), OR, CN, NO2, a C1-C6 thioether, a C1-C6 thioester group, an optionally substituted CO2R group, an optionally substituted COR group or an optionally substituted OCOR group (preferably R4 is H); R is H or an optionally substituted C1-C6 alkyl group; RHET is an optionally substituted heterocyclic group; and pharmaceutically acceptable salts, solvates or polymorphs thereof.

Optimization of diarylamines as non-nucleoside inhibitors of HIV-1 reverse transcriptase

Following computational analyses, potential non-nucleoside inhibitors of HIV-1 reverse transcriptase have been pursued through synthesis and assaying for anti-viral activity. The general class Het-NH-Ph-U has been considered, where Het is an aromatic heterocycle and U is an unsaturated, hydrophobic group. Results for compounds with Het = 2-thiazoyl and 2-pyrimidinyl are the focus of this report.

FUSED AZOLES SUCH AS 2,5-DISUBSTITUTED BENZIMIDAZOLES, BENZOXAZOLES AND BENZOTHIAZOLES AS KINASE INHIBITORS

The invention relates to compounds of the formulae (I) to (III) wherein the substituents are as defined in the specification. These compounds have kinase inhibitory activity, such as VEGFR/KDR inhibitory activity. Accordingly, the compounds of the formulae (I) to (III) would be useful in the prevention and treatment of angiogenesis related disorders, ophthalmological conditions, proliferative diseases, inflammatory diseases, and other pathological conditions as described in the specification.

Urotensin-II receptor antagonists

P51084 The present invention relates to sulfonamides, pharmaceutical compositions containing them, and their use as antagonists of urotensin II.