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Francois Tillequin - One of the best experts on this subject based on the ideXlab platform.
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troger s bases in the Acronycine benzo a Acronycine and benzo b Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and Cytotoxic Activity of Benzo[a]Acronycine and Benzo[b]Acronycine Substituted on the A Ring.
ChemInform, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Novel benzo[a]Acronycine (VIII) and benzo[b]Acronycine (IX) derivatives substituted in 10-position are synthesized following a similar strategy.
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Tröger’s bases in the Acronycine, benzo[a]Acronycine, and benzo[b]Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and cytotoxic activity of benzo[a]Acronycine and benzo[b]Acronycine substituted on the A ring.
European Journal of Medicinal Chemistry, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Abstract The impact of substitutions at position 10 in the A ring of the cytotoxic benzo[ a ]Acronycine and benzo[ b ]Acronycine series has been explored. 10-Bromobenzo[ a ] and 10-bromobenzo[ b ]Acronycine were prepared in 12% and 15% yield respectively from commercially available chemicals. Their 1,2-dihydro-1,2-dihydroxy diesters were synthesized. The different derivatives were tested against two cell lines KB-3-1 and L1210. Their cytotoxic activities were found in the same range of magnitude as their non-substituted counterparts. These structure–activity relationships permitted to conclude that the introduction of a substituent at position 10 maintains the activity in both the benzo[ a ] and [ b ]Acronycine series and open the way to further pharmacomodulations.
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Acronycine Derivatives: A Promising Series of Anti-Cancer Agents
Anti-Cancer Agents in Medicinal Chemistry, 2009Co-Authors: Quoc Chi Nguyen, Thomas Gaslonde, Hanh Dufat, Sylvie Michel, T. T. Nguyen, Rodrigue Yougnia, Francois TillequinAbstract:The pyranoacridone Acronycine (1) exhibits antitumor properties against a large panel of solid tumor models, but its moderate potency and low water solubility severely hampered the subsequent clinical trials. Development of synthetic analogues followed the isolation from several Sarcomelicope species of Acronycine epoxide (17), which led to a hypothesis of bioactivation of Acronycine by transformation of the 1,2-double bond into the corresponding oxirane. 1,2-Diacyloxy-1,2-dihydroAcronycine derivatives exhibited antitumor properties, with a broadened spectrum of activity and an increased potency. The demonstration that Acronycine interacted with DNA led to the development of benzo[a], [b], and [c]Acronycine analogs. 1,2-Dihydroxy-1,2-dihydrobenzo[b]Acronycine esters and diesters were active in human orthotopic models of cancers xenografted in nude mice. The activity of these compounds, exemplified by cis-1,2- diacetoxy-1,2-dihydrobenzo[b]Acronycine (49), developed in phase I clinical trials under the code S23906-1, was correlated with their ability to give covalent adducts with DNA, involving reaction between the N-2 amino group of guanines in the minor groove and the ester group at the benzylic position of the drug. The influence of the kinetics of DNA alkylation on the cytotoxic and antitumor properties showed a strong correlation between antiproliferative activity and DNA alkylation kinetics, with the most cytotoxic compounds, appearing as the slowest DNA alkylators. Hybrid compounds associating the acridone or benzo[b]acridone chromophore of Acronycine derivatives and the epoxyfuran alkylating unit present in psorospermin also displayed potent antiproliferative activities, alkylating DNA guanine units at position N-7 in the major groove, as natural xanthones belonging to the psorospermin series.
Sylvie Michel - One of the best experts on this subject based on the ideXlab platform.
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troger s bases in the Acronycine benzo a Acronycine and benzo b Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and Cytotoxic Activity of Benzo[a]Acronycine and Benzo[b]Acronycine Substituted on the A Ring.
ChemInform, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Novel benzo[a]Acronycine (VIII) and benzo[b]Acronycine (IX) derivatives substituted in 10-position are synthesized following a similar strategy.
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Tröger’s bases in the Acronycine, benzo[a]Acronycine, and benzo[b]Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and cytotoxic activity of benzo[a]Acronycine and benzo[b]Acronycine substituted on the A ring.
European Journal of Medicinal Chemistry, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Abstract The impact of substitutions at position 10 in the A ring of the cytotoxic benzo[ a ]Acronycine and benzo[ b ]Acronycine series has been explored. 10-Bromobenzo[ a ] and 10-bromobenzo[ b ]Acronycine were prepared in 12% and 15% yield respectively from commercially available chemicals. Their 1,2-dihydro-1,2-dihydroxy diesters were synthesized. The different derivatives were tested against two cell lines KB-3-1 and L1210. Their cytotoxic activities were found in the same range of magnitude as their non-substituted counterparts. These structure–activity relationships permitted to conclude that the introduction of a substituent at position 10 maintains the activity in both the benzo[ a ] and [ b ]Acronycine series and open the way to further pharmacomodulations.
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Acronycine Derivatives: A Promising Series of Anti-Cancer Agents
Anti-Cancer Agents in Medicinal Chemistry, 2009Co-Authors: Quoc Chi Nguyen, Thomas Gaslonde, Hanh Dufat, Sylvie Michel, T. T. Nguyen, Rodrigue Yougnia, Francois TillequinAbstract:The pyranoacridone Acronycine (1) exhibits antitumor properties against a large panel of solid tumor models, but its moderate potency and low water solubility severely hampered the subsequent clinical trials. Development of synthetic analogues followed the isolation from several Sarcomelicope species of Acronycine epoxide (17), which led to a hypothesis of bioactivation of Acronycine by transformation of the 1,2-double bond into the corresponding oxirane. 1,2-Diacyloxy-1,2-dihydroAcronycine derivatives exhibited antitumor properties, with a broadened spectrum of activity and an increased potency. The demonstration that Acronycine interacted with DNA led to the development of benzo[a], [b], and [c]Acronycine analogs. 1,2-Dihydroxy-1,2-dihydrobenzo[b]Acronycine esters and diesters were active in human orthotopic models of cancers xenografted in nude mice. The activity of these compounds, exemplified by cis-1,2- diacetoxy-1,2-dihydrobenzo[b]Acronycine (49), developed in phase I clinical trials under the code S23906-1, was correlated with their ability to give covalent adducts with DNA, involving reaction between the N-2 amino group of guanines in the minor groove and the ester group at the benzylic position of the drug. The influence of the kinetics of DNA alkylation on the cytotoxic and antitumor properties showed a strong correlation between antiproliferative activity and DNA alkylation kinetics, with the most cytotoxic compounds, appearing as the slowest DNA alkylators. Hybrid compounds associating the acridone or benzo[b]acridone chromophore of Acronycine derivatives and the epoxyfuran alkylating unit present in psorospermin also displayed potent antiproliferative activities, alkylating DNA guanine units at position N-7 in the major groove, as natural xanthones belonging to the psorospermin series.
Stephane Leonce - One of the best experts on this subject based on the ideXlab platform.
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Synthesis, Antitumor Activity, and Mechanism of Action of Benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one Analogs of Acronycine
Journal of Medicinal Chemistry, 2014Co-Authors: Wen Tian, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Laurence Kraus-berthier, Rodrigue Yougnia, Marie-hélène David-cordonnier, Sabine Depauw, Amélie Lansiaux, Hanh DufatAbstract:A series of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one (4), 13-aza derivatives of benzo[b]Acronycine, the isomeric 5-methoxy-2,2,13-trimethyl-2,13-dihydro-6H-benzo[b]chromeno[7,6-g][1,8]naphthyridin-6-one (5), and related cis-diols mono- and diesters were designed and synthesized. Their in vitro and in vivo biological activities were evaluated. As previously observed in the Acronycine series, esters were the most potent derivatives exhibiting submicromolar activities; among them monoesters are particularly active. Racemic diacetate 21 showed a strong activity against KB-3-1 cell lines and was selected for in vivo evaluation and proved to be active, inhibiting tumor growth by more than 80%. After separation of the two enantiomers, compounds 21a and 21b were also evaluated against C38 colon adenocarcinoma; their activities were found to be significantly different.
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troger s bases in the Acronycine benzo a Acronycine and benzo b Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and Cytotoxic Activity of Benzo[a]Acronycine and Benzo[b]Acronycine Substituted on the A Ring.
ChemInform, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Novel benzo[a]Acronycine (VIII) and benzo[b]Acronycine (IX) derivatives substituted in 10-position are synthesized following a similar strategy.
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Synthesis and cytotoxic activity of benzo[a]Acronycine and benzo[b]Acronycine substituted on the A ring.
European Journal of Medicinal Chemistry, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Abstract The impact of substitutions at position 10 in the A ring of the cytotoxic benzo[ a ]Acronycine and benzo[ b ]Acronycine series has been explored. 10-Bromobenzo[ a ] and 10-bromobenzo[ b ]Acronycine were prepared in 12% and 15% yield respectively from commercially available chemicals. Their 1,2-dihydro-1,2-dihydroxy diesters were synthesized. The different derivatives were tested against two cell lines KB-3-1 and L1210. Their cytotoxic activities were found in the same range of magnitude as their non-substituted counterparts. These structure–activity relationships permitted to conclude that the introduction of a substituent at position 10 maintains the activity in both the benzo[ a ] and [ b ]Acronycine series and open the way to further pharmacomodulations.
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Tröger’s bases in the Acronycine, benzo[a]Acronycine, and benzo[b]Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
Alain Pierré - One of the best experts on this subject based on the ideXlab platform.
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Synthesis, Antitumor Activity, and Mechanism of Action of Benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one Analogs of Acronycine
Journal of Medicinal Chemistry, 2014Co-Authors: Wen Tian, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Laurence Kraus-berthier, Rodrigue Yougnia, Marie-hélène David-cordonnier, Sabine Depauw, Amélie Lansiaux, Hanh DufatAbstract:A series of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one (4), 13-aza derivatives of benzo[b]Acronycine, the isomeric 5-methoxy-2,2,13-trimethyl-2,13-dihydro-6H-benzo[b]chromeno[7,6-g][1,8]naphthyridin-6-one (5), and related cis-diols mono- and diesters were designed and synthesized. Their in vitro and in vivo biological activities were evaluated. As previously observed in the Acronycine series, esters were the most potent derivatives exhibiting submicromolar activities; among them monoesters are particularly active. Racemic diacetate 21 showed a strong activity against KB-3-1 cell lines and was selected for in vivo evaluation and proved to be active, inhibiting tumor growth by more than 80%. After separation of the two enantiomers, compounds 21a and 21b were also evaluated against C38 colon adenocarcinoma; their activities were found to be significantly different.
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troger s bases in the Acronycine benzo a Acronycine and benzo b Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and Cytotoxic Activity of Benzo[a]Acronycine and Benzo[b]Acronycine Substituted on the A Ring.
ChemInform, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Novel benzo[a]Acronycine (VIII) and benzo[b]Acronycine (IX) derivatives substituted in 10-position are synthesized following a similar strategy.
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Tröger’s bases in the Acronycine, benzo[a]Acronycine, and benzo[b]Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and cytotoxic activity of benzo[a]Acronycine and benzo[b]Acronycine substituted on the A ring.
European Journal of Medicinal Chemistry, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Abstract The impact of substitutions at position 10 in the A ring of the cytotoxic benzo[ a ]Acronycine and benzo[ b ]Acronycine series has been explored. 10-Bromobenzo[ a ] and 10-bromobenzo[ b ]Acronycine were prepared in 12% and 15% yield respectively from commercially available chemicals. Their 1,2-dihydro-1,2-dihydroxy diesters were synthesized. The different derivatives were tested against two cell lines KB-3-1 and L1210. Their cytotoxic activities were found in the same range of magnitude as their non-substituted counterparts. These structure–activity relationships permitted to conclude that the introduction of a substituent at position 10 maintains the activity in both the benzo[ a ] and [ b ]Acronycine series and open the way to further pharmacomodulations.
Bruno Pfeiffer - One of the best experts on this subject based on the ideXlab platform.
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Synthesis, Antitumor Activity, and Mechanism of Action of Benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one Analogs of Acronycine
Journal of Medicinal Chemistry, 2014Co-Authors: Wen Tian, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Laurence Kraus-berthier, Rodrigue Yougnia, Marie-hélène David-cordonnier, Sabine Depauw, Amélie Lansiaux, Hanh DufatAbstract:A series of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one (4), 13-aza derivatives of benzo[b]Acronycine, the isomeric 5-methoxy-2,2,13-trimethyl-2,13-dihydro-6H-benzo[b]chromeno[7,6-g][1,8]naphthyridin-6-one (5), and related cis-diols mono- and diesters were designed and synthesized. Their in vitro and in vivo biological activities were evaluated. As previously observed in the Acronycine series, esters were the most potent derivatives exhibiting submicromolar activities; among them monoesters are particularly active. Racemic diacetate 21 showed a strong activity against KB-3-1 cell lines and was selected for in vivo evaluation and proved to be active, inhibiting tumor growth by more than 80%. After separation of the two enantiomers, compounds 21a and 21b were also evaluated against C38 colon adenocarcinoma; their activities were found to be significantly different.
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Synthesis, Antitumor Activity, and Mechanism of Action of Benzo[b]chromeno[6,5‑g][1,8]naphthyridin-7-one Analogs of Acronycine
2014Co-Authors: Wen Tian, Bruno Pfeiffer, Laurence Kraus-berthier, Rodrigue Yougnia, Sabine Depauw, Amélie Lansiaux, Marie-hélène David-cordonnier, Stéphane Léonce, Alain Pierré, Hanh DufatAbstract:A series of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one (4), 13-aza derivatives of benzo[b]Acronycine, the isomeric 5-methoxy-2,2,13-trimethyl-2,13-dihydro-6H-benzo[b]chromeno[7,6-g][1,8]naphthyridin-6-one (5), and related cis-diols mono- and diesters were designed and synthesized. Their in vitro and in vivo biological activities were evaluated. As previously observed in the Acronycine series, esters were the most potent derivatives exhibiting submicromolar activities; among them monoesters are particularly active. Racemic diacetate 21 showed a strong activity against KB-3-1 cell lines and was selected for in vivo evaluation and proved to be active, inhibiting tumor growth by more than 80%. After separation of the two enantiomers, compounds 21a and 21b were also evaluated against C38 colon adenocarcinoma; their activities were found to be significantly different
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troger s bases in the Acronycine benzo a Acronycine and benzo b Acronycine series
Tetrahedron Letters, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Francois TillequinAbstract:Abstract Reaction of 11-aminoAcronycine, 10-aminobenzo[ a ]Acronycine, and 10-aminobenzo[ b ]Acronycine with paraformaldehyde gave the corresponding Troger’s bases 11 , 14 , and 16 , respectively. The cytotoxic activity of those three new compounds was determined against L-1210 leukemia and KB-3-1 solid tumor cell lines, in comparison with their parent compounds, Acronycine, benzo[ a ]Acronycine, and benzo[ b ]Acronycine.
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Synthesis and Cytotoxic Activity of Benzo[a]Acronycine and Benzo[b]Acronycine Substituted on the A Ring.
ChemInform, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Novel benzo[a]Acronycine (VIII) and benzo[b]Acronycine (IX) derivatives substituted in 10-position are synthesized following a similar strategy.
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Synthesis and cytotoxic activity of benzo[a]Acronycine and benzo[b]Acronycine substituted on the A ring.
European Journal of Medicinal Chemistry, 2011Co-Authors: Thomas Gaslonde, Sylvie Michel, Bruno Pfeiffer, Stephane Leonce, Alain Pierré, Fabiola Covello, Laura Velazquez-alonso, Francois TillequinAbstract:Abstract The impact of substitutions at position 10 in the A ring of the cytotoxic benzo[ a ]Acronycine and benzo[ b ]Acronycine series has been explored. 10-Bromobenzo[ a ] and 10-bromobenzo[ b ]Acronycine were prepared in 12% and 15% yield respectively from commercially available chemicals. Their 1,2-dihydro-1,2-dihydroxy diesters were synthesized. The different derivatives were tested against two cell lines KB-3-1 and L1210. Their cytotoxic activities were found in the same range of magnitude as their non-substituted counterparts. These structure–activity relationships permitted to conclude that the introduction of a substituent at position 10 maintains the activity in both the benzo[ a ] and [ b ]Acronycine series and open the way to further pharmacomodulations.
