Tetrahydrocarbazole amides with potent activity against human papillomaviruses

Kristjan S. Gudmundsson; Sharon D. Boggs; Paul R. Sebahar; Leah D.Aurora Richardson; Andrew Spaltenstein; Pamela Golden; Phiroze B. Sethna; Kevin W. Brown; Kelly Moniri; Robert Harvey; Karen R. Romines

doi:10.1016/j.bmcl.2009.06.001

Tetrahydrocarbazole amides with potent activity against human papillomaviruses

Kristjan S. Gudmundsson, Sharon D. Boggs, Paul R. Sebahar, Leah D.Aurora Richardson, Andrew Spaltenstein, Pamela Golden, Phiroze B. Sethna, Kevin W. Brown, Kelly Moniri, Robert Harvey, Karen R. Romines

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

33 Scopus citations

Abstract

Synthesis of a series of tetrahydrocarbazole amides with potent activity against human papillomaviruses is described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole and the amide are outlined and resulting changes in antiviral activity and certain developability parameters are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the single digit nanomolar range were identified and N-[(1R)-6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide was selected for further evaluation.

Original language	English
Pages (from-to)	4110-4114
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2009.06.001
State	Published - 1 Aug 2009
Externally published	Yes

Keywords

Antiviral
Human papillomavirus
Tetrahydrocarbazole

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10.1016/j.bmcl.2009.06.001

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title = "Tetrahydrocarbazole amides with potent activity against human papillomaviruses",

abstract = "Synthesis of a series of tetrahydrocarbazole amides with potent activity against human papillomaviruses is described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole and the amide are outlined and resulting changes in antiviral activity and certain developability parameters are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the single digit nanomolar range were identified and N-[(1R)-6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide was selected for further evaluation.",

keywords = "Antiviral, Human papillomavirus, Tetrahydrocarbazole",

author = "Gudmundsson, {Kristjan S.} and Boggs, {Sharon D.} and Sebahar, {Paul R.} and Richardson, {Leah D.Aurora} and Andrew Spaltenstein and Pamela Golden and Sethna, {Phiroze B.} and Brown, {Kevin W.} and Kelly Moniri and Robert Harvey and Romines, {Karen R.}",

year = "2009",

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doi = "10.1016/j.bmcl.2009.06.001",

language = "English",

volume = "19",

pages = "4110--4114",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Tetrahydrocarbazole amides with potent activity against human papillomaviruses

AU - Gudmundsson, Kristjan S.

AU - Boggs, Sharon D.

AU - Sebahar, Paul R.

AU - Richardson, Leah D.Aurora

AU - Spaltenstein, Andrew

AU - Golden, Pamela

AU - Sethna, Phiroze B.

AU - Brown, Kevin W.

AU - Moniri, Kelly

AU - Harvey, Robert

AU - Romines, Karen R.

PY - 2009/8/1

Y1 - 2009/8/1

N2 - Synthesis of a series of tetrahydrocarbazole amides with potent activity against human papillomaviruses is described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole and the amide are outlined and resulting changes in antiviral activity and certain developability parameters are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the single digit nanomolar range were identified and N-[(1R)-6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide was selected for further evaluation.

AB - Synthesis of a series of tetrahydrocarbazole amides with potent activity against human papillomaviruses is described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole and the amide are outlined and resulting changes in antiviral activity and certain developability parameters are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the single digit nanomolar range were identified and N-[(1R)-6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide was selected for further evaluation.

KW - Antiviral

KW - Human papillomavirus

KW - Tetrahydrocarbazole

UR - http://www.scopus.com/inward/record.url?scp=67649965554&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2009.06.001

DO - 10.1016/j.bmcl.2009.06.001

M3 - Article

C2 - 19556128

AN - SCOPUS:67649965554

SN - 0960-894X

VL - 19

SP - 4110

EP - 4114

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 15

ER -

Tetrahydrocarbazole amides with potent activity against human papillomaviruses

Abstract

Keywords

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