SrasV1, PascalFrancis, Curation, bibRecord, 000991

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. V: 4-Substituted and 2,4-disubstituted analogs of nevirapine

Identifieur interne : 000991 ( PascalFrancis/Curation ); précédent : 000990; suivant : 000992

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. V: 4-Substituted and 2,4-disubstituted analogs of nevirapine

Auteurs : T. A. Kelly [États-Unis] ; J. R. Proudfoot ; D. W. Mcneil ; U. R. Patel ; E. David ; K. D. Hargrave ; P. M. Grob ; M. Cardozo ; A. Agarwal ; J. Adams

Source :

Journal of medicinal chemistry [ 0022-2623 ] ; 1995.

RBID : Pascal:96-0038342

Descripteurs français

Pascal (Inist)
- Relation structure activité, Antiviral, Inhibiteur enzyme, RNA-directed DNA polymerase, Névirapine, Résistance, Synthèse chimique, Hétérocycle azote, Composé tricyclique, Lactame, Dipyrido[3,2-b:2',3'-e][1,4]diazépin-6-one(4-[(4-aminophénoxy)méthyl]-11-cyclopropyl-5,6-dihydro), Dipyrido[3,2-b:2',3'-e][1,4]diazépin-6-one(11-cyclopropyl-5,6-dihydro-4-[(4-éthylaminophénoxy)méthyl]), Dipyridodiazépinone, Dipyridodiazépine dérivé, Composé non nucléoside.

English descriptors

KwdEn :
- Antiviral, Chemical synthesis, Enzyme inhibitor, Lactam, Nitrogen heterocycle, Nonnucleoside compound, RNA-directed DNA polymerase, Resistance, Structure activity relation, Tricyclic compound.

Abstract

Molecular modeling analysis of the recently published X-ray crystal structure of nevirapine bound to wild type human immunodeficiency virus type 1 reverse transcriptase (WT-RT) indicated the presence of a lipophilic cavity proximal to the 4-position of the inhibitor. A series of 4-substituted derivatives of nevirapine were thus synthesized to assess structure-activity relationships (SARs) and to see if increased binding to this region might translate into greater activity against mutant RTs. The results show that compounds with an appropriately spaced aryl ring appended to the 4-position of the dipyridodiazepinone ring system show good activity against WT-RT. Furthermore certain derivatives appear to inhibit the Y181C mutant RT. Attempts to combine these results with the recent discovery that 2-substituents enhance activity against the Y181C mutant led to a few compounds with moderate activity against both enzymes. The SAR of these two positions, however, could not be combined in a simple fashion.

A01	`01`	`1`		`@0 0022-2623`
A02	`01`			`@0 JMCMAR`
A03		`1`		`@0 J. med. chem.`
A05				`@2 38`
A06				`@2 24`
A08	`01`	`1`	`ENG`	`@1 Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. V: 4-Substituted and 2,4-disubstituted analogs of nevirapine`
A11	`01`	`1`		`@1 KELLY (T. A.)`
A11	`02`	`1`		`@1 PROUDFOOT (J. R.)`
A11	`03`	`1`		`@1 MCNEIL (D. W.)`
A11	`04`	`1`		`@1 PATEL (U. R.)`
A11	`05`	`1`		`@1 DAVID (E.)`
A11	`06`	`1`		`@1 HARGRAVE (K. D.)`
A11	`07`	`1`		`@1 GROB (P. M.)`
A11	`08`	`1`		`@1 CARDOZO (M.)`
A11	`09`	`1`		`@1 AGARWAL (A.)`
A11	`10`	`1`		`@1 ADAMS (J.)`
A14	`01`			`@1 Boehringer Ingelheim Pharmaceuticals Inc., res. development cent. @2 Ridgefield CT 06877 @3 USA`
A20				`@1 4839-4847`
A21				`@1 1995`
A23	`01`			`@0 ENG`
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A64	`01`	`1`		`@0 Journal of medicinal chemistry`
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C01	`01`		`ENG`	@0 Molecular modeling analysis of the recently published X-ray crystal structure of nevirapine bound to wild type human immunodeficiency virus type 1 reverse transcriptase (WT-RT) indicated the presence of a lipophilic cavity proximal to the 4-position of the inhibitor. A series of 4-substituted derivatives of nevirapine were thus synthesized to assess structure-activity relationships (SARs) and to see if increased binding to this region might translate into greater activity against mutant RTs. The results show that compounds with an appropriately spaced aryl ring appended to the 4-position of the dipyridodiazepinone ring system show good activity against WT-RT. Furthermore certain derivatives appear to inhibit the Y181C mutant RT. Attempts to combine these results with the recent discovery that 2-substituents enhance activity against the Y181C mutant led to a few compounds with moderate activity against both enzymes. The SAR of these two positions, however, could not be combined in a simple fashion.
C02	`01`	`X`		`@0 002B02S05`
C03	`01`	`X`	`FRE`	`@0 Relation structure activité @5 01`
C03	`01`	`X`	`ENG`	`@0 Structure activity relation @5 01`
C03	`01`	`X`	`SPA`	`@0 Relación estructura actividad @5 01`
C03	`02`	`X`	`FRE`	`@0 Antiviral @5 02`
C03	`02`	`X`	`ENG`	`@0 Antiviral @5 02`
C03	`02`	`X`	`SPA`	`@0 Antiviral @5 02`
C03	`03`	`X`	`FRE`	`@0 Inhibiteur enzyme @5 03`
C03	`03`	`X`	`ENG`	`@0 Enzyme inhibitor @5 03`
C03	`03`	`X`	`SPA`	`@0 Inhibidor enzima @5 03`
C03	`04`	`X`	`FRE`	`@0 RNA-directed DNA polymerase @2 FE @5 04`
C03	`04`	`X`	`ENG`	`@0 RNA-directed DNA polymerase @2 FE @5 04`
C03	`04`	`X`	`SPA`	`@0 RNA-directed DNA polymerase @2 FE @5 04`
C03	`05`	`X`	`FRE`	`@0 Névirapine @2 NK @2 FR @5 05`
C03	`06`	`X`	`FRE`	`@0 Résistance @5 06`
C03	`06`	`X`	`ENG`	`@0 Resistance @5 06`
C03	`06`	`X`	`SPA`	`@0 Resistencia @5 06`
C03	`07`	`X`	`FRE`	`@0 Synthèse chimique @5 07`
C03	`07`	`X`	`ENG`	`@0 Chemical synthesis @5 07`
C03	`07`	`X`	`GER`	`@0 Chemische Synthese @5 07`
C03	`07`	`X`	`SPA`	`@0 Síntesis química @5 07`
C03	`08`	`X`	`FRE`	`@0 Hétérocycle azote @5 08`
C03	`08`	`X`	`ENG`	`@0 Nitrogen heterocycle @5 08`
C03	`08`	`X`	`SPA`	`@0 Heterociclo nitrógeno @5 08`
C03	`09`	`X`	`FRE`	`@0 Composé tricyclique @5 09`
C03	`09`	`X`	`ENG`	`@0 Tricyclic compound @5 09`
C03	`09`	`X`	`SPA`	`@0 Compuesto tricíclico @5 09`
C03	`10`	`X`	`FRE`	`@0 Lactame @5 10`
C03	`10`	`X`	`ENG`	`@0 Lactam @5 10`
C03	`10`	`X`	`SPA`	`@0 Lactamo @5 10`
C03	`11`	`X`	`FRE`	`@0 Dipyrido[3,2-b:2',3'-e][1,4]diazépin-6-one(4-[(4-aminophénoxy)méthyl]-11-cyclopropyl-5,6-dihydro) @2 NK @2 FR @4 INC @5 62`
C03	`12`	`X`	`FRE`	`@0 Dipyrido[3,2-b:2',3'-e][1,4]diazépin-6-one(11-cyclopropyl-5,6-dihydro-4-[(4-éthylaminophénoxy)méthyl]) @2 NK @2 FR @4 INC @5 63`
C03	`13`	`X`	`FRE`	`@0 Dipyridodiazépinone @4 INC @5 64`
C03	`14`	`X`	`FRE`	`@0 Dipyridodiazépine dérivé @4 INC @5 65`
C03	`15`	`X`	`FRE`	`@0 Composé non nucléoside @4 CD @5 96`
C03	`15`	`X`	`ENG`	`@0 Nonnucleoside compound @4 CD @5 96`
C07	`01`	`X`	`FRE`	`@0 Nucleotidyltransferases @2 FE`
C07	`01`	`X`	`ENG`	`@0 Nucleotidyltransferases @2 FE`
C07	`01`	`X`	`SPA`	`@0 Nucleotidyltransferases @2 FE`
C07	`02`	`X`	`FRE`	`@0 Transferases @2 FE`
C07	`02`	`X`	`ENG`	`@0 Transferases @2 FE`
C07	`02`	`X`	`SPA`	`@0 Transferases @2 FE`
C07	`03`	`X`	`FRE`	`@0 Enzyme`
C07	`03`	`X`	`ENG`	`@0 Enzyme`
C07	`03`	`X`	`SPA`	`@0 Enzima`
N21				`@1 015`

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Pascal:96-0038342

Le document en format XML

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<term>RNA-directed DNA polymerase</term>
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<term>Hétérocycle azote</term>
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<front><div type="abstract" xml:lang="en">Molecular modeling analysis of the recently published X-ray crystal structure of nevirapine bound to wild type human immunodeficiency virus type 1 reverse transcriptase (WT-RT) indicated the presence of a lipophilic cavity proximal to the 4-position of the inhibitor. A series of 4-substituted derivatives of nevirapine were thus synthesized to assess structure-activity relationships (SARs) and to see if increased binding to this region might translate into greater activity against mutant RTs. The results show that compounds with an appropriately spaced aryl ring appended to the 4-position of the dipyridodiazepinone ring system show good activity against WT-RT. Furthermore certain derivatives appear to inhibit the Y181C mutant RT. Attempts to combine these results with the recent discovery that 2-substituents enhance activity against the Y181C mutant led to a few compounds with moderate activity against both enzymes. The SAR of these two positions, however, could not be combined in a simple fashion.</div>
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<fA11 i1="01" i2="1"><s1>KELLY (T. A.)</s1>
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<fC01 i1="01" l="ENG"><s0>Molecular modeling analysis of the recently published X-ray crystal structure of nevirapine bound to wild type human immunodeficiency virus type 1 reverse transcriptase (WT-RT) indicated the presence of a lipophilic cavity proximal to the 4-position of the inhibitor. A series of 4-substituted derivatives of nevirapine were thus synthesized to assess structure-activity relationships (SARs) and to see if increased binding to this region might translate into greater activity against mutant RTs. The results show that compounds with an appropriately spaced aryl ring appended to the 4-position of the dipyridodiazepinone ring system show good activity against WT-RT. Furthermore certain derivatives appear to inhibit the Y181C mutant RT. Attempts to combine these results with the recent discovery that 2-substituents enhance activity against the Y181C mutant led to a few compounds with moderate activity against both enzymes. The SAR of these two positions, however, could not be combined in a simple fashion.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>002B02S05</s0>
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<fC03 i1="01" i2="X" l="FRE"><s0>Relation structure activité</s0>
<s5>01</s5>
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<fC03 i1="01" i2="X" l="ENG"><s0>Structure activity relation</s0>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Relación estructura actividad</s0>
<s5>01</s5>
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<s5>02</s5>
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<fC03 i1="02" i2="X" l="ENG"><s0>Antiviral</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Antiviral</s0>
<s5>02</s5>
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<fC03 i1="03" i2="X" l="FRE"><s0>Inhibiteur enzyme</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Enzyme inhibitor</s0>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Inhibidor enzima</s0>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>RNA-directed DNA polymerase</s0>
<s2>FE</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>RNA-directed DNA polymerase</s0>
<s2>FE</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>RNA-directed DNA polymerase</s0>
<s2>FE</s2>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Névirapine</s0>
<s2>NK</s2>
<s2>FR</s2>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Résistance</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Resistance</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Resistencia</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Synthèse chimique</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Chemical synthesis</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="GER"><s0>Chemische Synthese</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Síntesis química</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Hétérocycle azote</s0>
<s5>08</s5>
</fC03>
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<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Composé tricyclique</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Tricyclic compound</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Compuesto tricíclico</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Lactame</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Lactam</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Lactamo</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Dipyrido[3,2-b:2',3'-e][1,4]diazépin-6-one(4-[(4-aminophénoxy)méthyl]-11-cyclopropyl-5,6-dihydro)</s0>
<s2>NK</s2>
<s2>FR</s2>
<s4>INC</s4>
<s5>62</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Dipyrido[3,2-b:2',3'-e][1,4]diazépin-6-one(11-cyclopropyl-5,6-dihydro-4-[(4-éthylaminophénoxy)méthyl])</s0>
<s2>NK</s2>
<s2>FR</s2>
<s4>INC</s4>
<s5>63</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Dipyridodiazépinone</s0>
<s4>INC</s4>
<s5>64</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Dipyridodiazépine dérivé</s0>
<s4>INC</s4>
<s5>65</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Composé non nucléoside</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Nonnucleoside compound</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Nucleotidyltransferases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Nucleotidyltransferases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Nucleotidyltransferases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Transferases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Transferases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Transferases</s0>
<s2>FE</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE"><s0>Enzyme</s0>
</fC07>
<fC07 i1="03" i2="X" l="ENG"><s0>Enzyme</s0>
</fC07>
<fC07 i1="03" i2="X" l="SPA"><s0>Enzima</s0>
</fC07>
<fN21><s1>015</s1>
</fN21>
</pA>
</standard>
</inist>
</record>

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   |texte=   Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. V: 4-Substituted and 2,4-disubstituted analogs of nevirapine
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Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. V: 4-Substituted and 2,4-disubstituted analogs of nevirapine

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. V: 4-Substituted and 2,4-disubstituted analogs of nevirapine

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