5-Chloro-3-(3,5-dimethyl-benzenesulfonyl)-1H-indole-2-carboxylic acid amide

ID: ALA85059

Chembl Id: CHEMBL85059

Cas Number: 473257-93-1

PubChem CID: 506873

Max Phase: Preclinical

Molecular Formula: C17H15ClN2O3S

Molecular Weight: 362.84

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(S(=O)(=O)c2c(C(N)=O)[nH]c3ccc(Cl)cc23)c1

Standard InChI:  InChI=1S/C17H15ClN2O3S/c1-9-5-10(2)7-12(6-9)24(22,23)16-13-8-11(18)3-4-14(13)20-15(16)17(19)21/h3-8,20H,1-2H3,(H2,19,21)

Standard InChI Key:  GXWODWMYKXULHQ-UHFFFAOYSA-N

Associated Targets(Human)

MT4 (17854 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C8166 (1658 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEL (6614 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Human immunodeficiency virus 1 (70413 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pol Human immunodeficiency virus type 1 protease (9113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human immunodeficiency virus 2 (5592 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vesicular stomatitis virus (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Respiratory syncytial virus (3434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Coxsackievirus B4 (2249 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human respirovirus 3 (1674 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mammalian orthoreovirus 1 (1523 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sindbis virus (1599 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Punta Toro virus (1491 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human alphaherpesvirus 1 (11089 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Human alphaherpesvirus 2 (4932 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vaccinia virus (4609 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Influenza A virus (11224 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Influenza A virus H3N2 (588 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Influenza B virus (2113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Feline coronavirus (624 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Felid alphaherpesvirus 1 (460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 362.84Molecular Weight (Monoisotopic): 362.0492AlogP: 3.37#Rotatable Bonds: 3
Polar Surface Area: 93.02Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 9.56CX Basic pKa: CX LogP: 3.43CX LogD: 3.43
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.75Np Likeness Score: -1.03

References

1. Silvestri R, De Martino G, La Regina G, Artico M, Massa S, Vargiu L, Mura M, Loi AG, Marceddu T, La Colla P..  (2003)  Novel indolyl aryl sulfones active against HIV-1 carrying NNRTI resistance mutations: synthesis and SAR studies.,  46  (12): [PMID:12773052] [10.1021/jm0211063]
2. Silvestri R, Artico M, De Martino G, La Regina G, Loddo R, La Colla M, Mura M, La Colla P..  (2004)  Simple, short peptide derivatives of a sulfonylindolecarboxamide (L-737,126) active in vitro against HIV-1 wild type and variants carrying non-nucleoside reverse transcriptase inhibitor resistance mutations.,  47  (15): [PMID:15239667] [10.1021/jm031147e]
3. Ragno R, Artico M, De Martino G, La Regina G, Coluccia A, Di Pasquali A, Silvestri R..  (2005)  Docking and 3-D QSAR studies on indolyl aryl sulfones. Binding mode exploration at the HIV-1 reverse transcriptase non-nucleoside binding site and design of highly active N-(2-hydroxyethyl)carboxamide and N-(2-hydroxyethyl)carbohydrazide derivatives.,  48  (1): [PMID:15634015] [10.1021/jm040854k]
4. Ragno R, Coluccia A, La Regina G, De Martino G, Piscitelli F, Lavecchia A, Novellino E, Bergamini A, Ciaprini C, Sinistro A, Maga G, Crespan E, Artico M, Silvestri R..  (2006)  Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide.,  49  (11): [PMID:16722636] [10.1021/jm0512490]
5. Piscitelli F, Coluccia A, Brancale A, La Regina G, Sansone A, Giordano C, Balzarini J, Maga G, Zanoli S, Samuele A, Cirilli R, La Torre F, Lavecchia A, Novellino E, Silvestri R..  (2009)  Indolylarylsulfones bearing natural and unnatural amino acids. Discovery of potent inhibitors of HIV-1 non-nucleoside wild type and resistant mutant strains reverse transcriptase and coxsackie B4 virus.,  52  (7): [PMID:19281225] [10.1021/jm801470b]
6. Huang B, Wang X, Liu X, Chen Z, Li W, Sun S, Liu H, Daelemans D, De Clercq E, Pannecouque C, Zhan P, Liu X..  (2017)  Discovery of novel DAPY-IAS hybrid derivatives as potential HIV-1 inhibitors using molecular hybridization based on crystallographic overlays.,  25  (16): [PMID:28659246] [10.1016/j.bmc.2017.06.022]
7. Zhao T, Meng Q, Kang D, Ji J, De Clercq E, Pannecouque C, Liu X, Zhan P..  (2019)  Discovery of novel indolylarylsulfones as potent HIV-1 NNRTIs via structure-guided scaffold morphing.,  182  [PMID:31434039] [10.1016/j.ejmech.2019.111619]
8. Gao P,Song S,Frutos-Beltrán E,Li W,Sun B,Kang D,Zou J,Zhang J,Pannecouque C,De Clercq E,Menéndez-Arias L,Zhan P,Liu X.  (2021)  Novel indolylarylsulfone derivatives as covalent HIV-1 reverse transcriptase inhibitors specifically targeting the drug-resistant mutant Y181C.,  30  [PMID:33352387] [10.1016/j.bmc.2020.115927]
9. Nalli M,Armijos Rivera JI,Masci D,Coluccia A,Badia R,Riveira-Muñoz E,Brambilla A,Cinquina E,Turriziani O,Falasca F,Catalano M,Limatola C,Esté JA,Maga G,Silvestri R,Crespan E,La Regina G.  (2020)  New indolylarylsulfone non-nucleoside reverse transcriptase inhibitors show low nanomolar inhibition of single and double HIV-1 mutant strains.,  208  [PMID:32883642] [10.1016/j.ejmech.2020.112696]
10. Gao S, Cheng Y, Song S, Song L, Zhao F, Xu S, Kang D, Sun L, Gao P, De Clercq E, Pannecouque C, Liu X, Zhan P..  (2022)  Chemical space exploration around indolylarylsulfone scaffold led to a novel class of highly active HIV-1 NNRTIs with spiro structural features.,  238  [PMID:35640327] [10.1016/j.ejmech.2022.114471]
11. Xu S, Song S, Sun L, Gao P, Gao S, Ma Y, Kang D, Cheng Y, Zhang X, Cherukupalli S, De Clercq E, Pannecouque C, Liu X, Zhan P..  (2022)  Indolylarylsulfones bearing phenylboronic acid and phenylboronate ester functionalities as potent HIV‑1 non-nucleoside reverse transcriptase inhibitors.,  53  [PMID:34890994] [10.1016/j.bmc.2021.116531]

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