352548-47-1

Basic information

• Product Name: 1H-Pyrido[3,2-b]indole-3-carbonitrile, 2,5-dihydro-5-methyl-1-(4-nitrophenyl)-2-oxo-
• Synonyms: CBL-4*1;5-methyl-1-(4-nitro-phenyl)-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indole-3-carbonitrile;NcRTI-1;5-methyl-1-(4-nitrophenyl)-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indole-3-carbonitrile
• CAS NO: 352548-47-1
• Molecular Formula: C19H12N4O3
• Molecular Weight: 344.329
• Mol File: 352548-47-1.mol

Chemical Properties

• Boiling Point: 618.7±55.0 °C(Predicted)
• Density: 1.40±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1H-Pyrido[3,2-b]indole-3-carbonitrile, 2,5-dihydro-5-methyl-1-(4-nitrophenyl)-2-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrido[3,2-b]indole-3-carbonitrile, 2,5-dihydro-5-methyl-1-(4-nitrophenyl)-2-oxo-(352548-47-1)
• EPA Substance Registry System: 1H-Pyrido[3,2-b]indole-3-carbonitrile, 2,5-dihydro-5-methyl-1-(4-nitrophenyl)-2-oxo-(352548-47-1)

Safety Data

• Hazardous Substances Data: 352548-47-1(Hazardous Substances Data)

Usage

Heterocyclic compound

Contains a pyridine ring fused to an indole ring

Functional groups

Carbonitrile

Substituents

Nitrophenyl group, methyl group

Usage

Research and pharmaceutical applications due to potential biological activities

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 167954-14-5 3-[N-(4-nitrophenyl)amino]-2-formylindole 
• 167954-19-0 3-[N-(4-nitrophenyl)amino]indole 
• 100-01-6 4-nitro-aniline 
• 67766-00-1 N-acetyl-3-p-nitrophenylaminoindole 
• 33025-60-4 1-(3-hydroxy-1H-indol-1-yl)ethanone 
• 304465-35-8 1-(4-nitrophenyl)-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indole-3-carbonitrile 
• 74-88-4 methyl iodide 

Downstream Products

• 698397-11-4 C₁₉H₁₄N₄O 
• 698396-93-9 C₁₉H₁₅N₅O₄ 
• 869791-85-5 8-bromo-5-methyl-1-(4-nitro-phenyl)-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indole-3-carbonitrile 
• 698396-95-1 5-methyl-1-(4-nitrophenyl)-3-(5-trifluoromethyl-[1,2,4]oxadiazol-3-yl)-1,5-dihydro-pyrido[3,2-b]indol-2-one 
• 698396-96-2 C₂₀H₁₃N₅O₄S 
• 698396-87-1 C₂₀H₁₃N₅O₅ 
• 698396-85-9 C₂₁H₁₄N₆O 
• 698396-84-8 C₂₃H₁₆N₄O 

Relevant articles and documents

PROCESS FOR PREPARING 2-OXO-2,5-DIHYDRO-1H-PYRIDO[3,2-B]INDOLE-3-CARBONITRILES

A process for preparing 2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indole-3-carbonitriles starting from 1-substituted indole-2-carboxaldehyde with an aromatic amine and reacting the thus obtained intermediate with a cyanoacetic acid ester.

4-SUBSTITUTED-1,5-DIHYDRO-PYRIDO[3,2-B]INDOL-2-ONES

4-substituted 1,5-dihydro-pyrido[3,2-b]indol-2-ones of formula (I): the N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein n is 1, 2 or 3; R1 is hydrogen, cyano, halo, substituted carbonyl, methanimidamidyl, N-hydroxymethanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, Het1 or Het2; X is NR 2, O, S, SO, SO2; R2 is hydrogen, C 1-10alkyl, C2-10alkenyl, C 3-7cycloalkyl, which are optionally substituted; R2 is aryl substituted with -COOR4 ; or R2 is: (b-1); (b-2); -CpH2p-CH(OR14 )-CqH 2q-R15(b-3); -CH2-CH2-(O-CH2-CH2)m-OR14 (b-4); -CH2-CH2-(O-CH2-CH2)m-NR5aR5b(b-5); -a1=a2-a3=a4- is -CH=CH-CH=CH-; -N=CH-CH=CH-; -CH=N-CH=CH-; -CH=CH-N=CH-; -CH=CH-CH=N-; wherein hydrogen atoms in (c-1) - (c-5) may be replaced by certain radicals; R3 is obtionally substituted phenyl or a monocyclic or bicyclic aromatic heterocyclic ring system that can be substituted; R21 is halo, hydroxy, amino, carboxyl, C1-6alkyl, C3-7cycloalkyl, arylC1-6alkyl, formyl, C1-6alkylcarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonylo xy, -C(=O)-NR13R14; C1-6alkyloxy, arylC1-6alkyloxy, polyhaloC1-6alkyloxy, amino, mono or di(C1-6alkyl)amino, formylamino, C1-6alkylcarbonylamino, C1-6alkylsulfo nylamino, mercapto, C1-6alkylthio, arylthio, aryloxy, arylC1-6alkylthio, C1-6alkylsulfynyl, C1-6alkylsulfo nyl, aryl, arylamino, Het1, Het2.

6,7,8,9-SUBSTITUTED 1-PHENYL-1,5-DIHYDRO-PYRIDO[3,2-B]INDOL-2-ONES USEFUL AS ANTI-INFECTIVE PHARMACEUTICAL AGENTS

This invention concerns the compounds (I); the N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein X is NR2, O, S, SO, SO2; R1 is hydrogen, cyano, halo, substituted carbonyl, methanimidamidyl, N-hydroxy-methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, Het1 or Het2; n is 1, 2 or 3; R2 is hydrogen, aryl substituted with a radical -COOR4; or R2 is substituted C1-10alkyl,C2-10alkenyl or C3-7cycloalkyl; or R2 is a radical of formula: (b-1); (b-2); -CpH2p-CH(OR14)-CqH2q-R15 (b-3); -CH2-CH2-(O-CH2-CH2)m-OR14 (b-4); -CH2-CH2-(O-CH2-CH2)m-NR5aR5b (b-5); -a1=a2-a3=a4- is -CH=CH-CH=CH- ; -N=CH-CH=CH- ;-CH=N-CH=CH- ; -CH=CH- N=CH- ; -CH=CH-CH=N- (c-5); wherein one of the hydrogen atoms in (c-1) - (c-5) is replaced by particular radicals; R3 is nitro, cyano, amino, halo, hydroxy, C1-4alkyloxy, hydroxycarbonyl, substituted carbonyl, methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, N-hydroxy- methanimidamidyl or Het1.

COMBINATIONS OF SUBSTITUTED 1-PHENYL-1,5-DIHYDRO-PYRIDO- [3,2-B] INDOL-2-ONES AND OTHER HIV INHIBITORS

The present invention concerns combinations comprising a compound of formula (I); the N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters or metabolites thereof, wherein n is 1, 2 or 3; R1 is H, CN, halo, aminoC(=O), C(=O)OH, C1-4alkyloxyC(=O), C1-4 alkylC(=O), mono- or di(C1-4alkyl)aminoC(=O), arylaminoC(=O), N-(aryl)-N-(C1-4 alkyl)aminoC(=O), methanimidamidyl,N-hydroxy-methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, Het1 or Het2; R2 is H, C1-10alkyl, C2-10alkenyl, C3-7cycloalkyl, wherein said C1-10alkyl, C2-10alkenyl and C3-7 cycloalkyl may be optionally substituted; R3 is nitro, cyano, amino, halo, hydroxy, C1-4alkyloxy, hydroxyC(=O), aminoC(=O), C1-4alkyloxyC(=O), mono- or di(C1-4alkyl)aminoC(=O), C1-4alkylC(=O), methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl,N-hydroxy-methanimidamidyl or Het1; and another HIV inhibitor. The invention also concerns products comprising a compound of formula (I) and another HIV inhibitor, as a combined preparation for simultaneous, separate or sequential use in treatment of retroviral infections such as HIV infection, in particular, in the treatment of infections with multi-drug resistant retroviruses.

SUBSTITUTED INDOLEPYRIDINIUM AS ANTI-INFECTIVE COMPOUNDS

The present invention concerns the compounds of formula (I) their N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites, wherein n is 1, 2 or 3; R1is H, CN, halo, aminoC(=O), C(=O)OH, C1-4alkyloxyC(=O), C1-4alkylC(=O), mono- or di(C1-4alkyl)aminoC(=O), arylaminoC(=O), N-(aryl)-N-(C1-4alkyl)aminoC(=O), methanimidamidyl, N-hydroxy-methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, Het1 or Het2; R2 is H, C1-10alkyl, C2-10alkenyl, C3-7cycloalkyl, wherein said C1-10alkyl, C2-10alkenyl and C3-7cycloalkyl may be optionally substituted; R3 is nitro, cyano, amino, halo, hydroxy, C1-4alkyloxy, hydroxyC(=O), aminoC(=O), C1-4alkyloxyC(=O), mono- or di(C1-4alkyl)aminoC(=O), C1-4alkylC(=O), methanimidamidyl, mono- or di(C1-4alkyl)methanimidamidyl, N-hydroxy-methanimidamidyl or Het1; for use as a medicine. The invention further relates to a novel subgroup of the compounds of formula (I), and to compositions comprising compounds of formula (I)