Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide

Rino Ragno; Antonio Coluccia; Giuseppe La Regina; Gabriella De Martino; Francesco Piscitelli; Antonio Lavecchia; Ettore Novellino; Alberto Bergamini; Chiara Ciaprini; Anna Sinistro; Giovanni Maga; Emanuele Crespan; Marino Artico; Romano Silvestri

doi:10.1021/jm0512490

Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide

Rino Ragno, Antonio Coluccia, Giuseppe La Regina, Gabriella De Martino, Francesco Piscitelli, Antonio Lavecchia, Ettore Novellino, Alberto Bergamini, Chiara Ciaprini, Anna Sinistro, Giovanni Maga, Emanuele Crespan, Marino Artico, Romano Silvestri

Istituto Dermopatico dell'Immacolata , IDI

Research output: Contribution to journal › Article › peer-review

Abstract

Molecular modeling studies and an updated highly predictive 3-D QSAR model led to the discovery of exceptionally potent indolyl aryl sulfones (IASs) characterized by the presence of either a pyrrolidyn-2-one nucleus at the indole-2-carboxamide or some substituents at the indole-2-carbohydrazide. Compounds 7 and 9 were found active in the sub-nanomolar range of concentration in both MT-4 and C8166 cell-based anti-HIV assays. These compounds, and in particular compound 9, also showed excellent inhibitory activity against both HIV-112 and HIV-AB1 primary isolates in lymphocytes and against HIV WT in macrophages.

Original language	English
Pages (from-to)	3172-3184
Number of pages	13
Journal	Journal of Medicinal Chemistry
Volume	49
Issue number	11
DOIs	https://doi.org/10.1021/jm0512490
Publication status	Published - Jun 1 2006

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jm0512490

Cite this

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. Journal of Medicinal Chemistry, 49(11), 3172-3184. https://doi.org/10.1021/jm0512490

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', Journal of Medicinal Chemistry, vol. 49, no. 11, pp. 3172-3184. https://doi.org/10.1021/jm0512490

@article{e38fccb7fdda4f6fa8890c2bf46cd340,

title = "Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide",

abstract = "Molecular modeling studies and an updated highly predictive 3-D QSAR model led to the discovery of exceptionally potent indolyl aryl sulfones (IASs) characterized by the presence of either a pyrrolidyn-2-one nucleus at the indole-2-carboxamide or some substituents at the indole-2-carbohydrazide. Compounds 7 and 9 were found active in the sub-nanomolar range of concentration in both MT-4 and C8166 cell-based anti-HIV assays. These compounds, and in particular compound 9, also showed excellent inhibitory activity against both HIV-112 and HIV-AB1 primary isolates in lymphocytes and against HIV WT in macrophages.",

author = "Rino Ragno and Antonio Coluccia and {La Regina}, Giuseppe and {De Martino}, Gabriella and Francesco Piscitelli and Antonio Lavecchia and Ettore Novellino and Alberto Bergamini and Chiara Ciaprini and Anna Sinistro and Giovanni Maga and Emanuele Crespan and Marino Artico and Romano Silvestri",

year = "2006",

month = jun,

day = "1",

doi = "10.1021/jm0512490",

language = "English",

volume = "49",

pages = "3172--3184",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide

AU - Ragno, Rino

AU - Coluccia, Antonio

AU - La Regina, Giuseppe

AU - De Martino, Gabriella

AU - Piscitelli, Francesco

AU - Lavecchia, Antonio

AU - Novellino, Ettore

AU - Bergamini, Alberto

AU - Ciaprini, Chiara

AU - Sinistro, Anna

AU - Maga, Giovanni

AU - Crespan, Emanuele

AU - Artico, Marino

AU - Silvestri, Romano

PY - 2006/6/1

Y1 - 2006/6/1

N2 - Molecular modeling studies and an updated highly predictive 3-D QSAR model led to the discovery of exceptionally potent indolyl aryl sulfones (IASs) characterized by the presence of either a pyrrolidyn-2-one nucleus at the indole-2-carboxamide or some substituents at the indole-2-carbohydrazide. Compounds 7 and 9 were found active in the sub-nanomolar range of concentration in both MT-4 and C8166 cell-based anti-HIV assays. These compounds, and in particular compound 9, also showed excellent inhibitory activity against both HIV-112 and HIV-AB1 primary isolates in lymphocytes and against HIV WT in macrophages.

AB - Molecular modeling studies and an updated highly predictive 3-D QSAR model led to the discovery of exceptionally potent indolyl aryl sulfones (IASs) characterized by the presence of either a pyrrolidyn-2-one nucleus at the indole-2-carboxamide or some substituents at the indole-2-carbohydrazide. Compounds 7 and 9 were found active in the sub-nanomolar range of concentration in both MT-4 and C8166 cell-based anti-HIV assays. These compounds, and in particular compound 9, also showed excellent inhibitory activity against both HIV-112 and HIV-AB1 primary isolates in lymphocytes and against HIV WT in macrophages.

UR - http://www.scopus.com/inward/record.url?scp=33744831188&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33744831188&partnerID=8YFLogxK

U2 - 10.1021/jm0512490

DO - 10.1021/jm0512490

M3 - Article

C2 - 16722636

AN - SCOPUS:33744831188

SN - 0022-2623

VL - 49

SP - 3172

EP - 3184

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 11

ER -

Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this