Efficient synthesis of 16 aromatic Morita–Baylis–Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi
We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on L. Amazonensis and L. chagasi and a relationship between the chemical structure and biological activity (S.A.R.). Sixteen aromatic Morita–Baylis–Hillman adducts (MBHA) 1– 16 wer...
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| Published in: | Bioorganic chemistry Vol. 38; no. 6; pp. 279 - 284 |
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| Main Authors: | , , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Inc
01-12-2010
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| Abstract | We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on
L. Amazonensis and
L. chagasi and a relationship between the chemical structure and biological activity (S.A.R.).
Sixteen aromatic Morita–Baylis–Hillman adducts (MBHA)
1–
16 were efficiently synthesized in a one step Morita–Baylis–Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81–100% yields) without the formation of side products on DABCO catalysis and at low temperature (0
°C). The toxicities of these compounds were assessed against promastigote form of
Leishmania amazonensis and
Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for
14 and
16 (IC
50 values of 6.88
μg
mL
−1 and 11.06
μg
mL
−1 respectively on
L.
amazonensis; 9.58
μg
mL
−1 and 14.34
μg
mL
−1 respectively on
L.
chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds. |
|---|---|
| AbstractList | Sixteen aromatic Morita-Baylis-Hillman adducts (MBHA) 1-16 were efficiently synthesized in a one step Morita-Baylis-Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81-100% yields) without the formation of side products on DABCO catalysis and at low temperature (0°C). The toxicities of these compounds were assessed against promastigote form of Leishmania amazonensis and Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for 14 and 16 (IC₅₀ values of 6.88μgmL⁻¹ and 11.06μgmL⁻¹ respectively on L. amazonensis; 9.58μgmL⁻¹ and 14.34μgmL⁻¹ respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds. We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on L. Amazonensis and L. chagasi and a relationship between the chemical structure and biological activity (S.A.R.). Sixteen aromatic Morita–Baylis–Hillman adducts (MBHA) 1– 16 were efficiently synthesized in a one step Morita–Baylis–Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81–100% yields) without the formation of side products on DABCO catalysis and at low temperature (0 °C). The toxicities of these compounds were assessed against promastigote form of Leishmania amazonensis and Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for 14 and 16 (IC 50 values of 6.88 μg mL −1 and 11.06 μg mL −1 respectively on L. amazonensis; 9.58 μg mL −1 and 14.34 μg mL −1 respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds. Sixteen aromatic Morita-Baylis-Hillman adducts (MBHA) 1- 16 were efficiently synthesized in a one step Morita-Baylis-Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81-100% yields) without the formation of side products on DABCO catalysis and at low temperature (0 C). The toxicities of these compounds were assessed against promastigote form of Leishmania amazonensis and Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for 14 and 16 (IC sub(50) values of 6.88 kg mL super(-1) and 11.06 kg mL super(-1) respectively on L. amazonensis; 9.58 kg mL super(-1) and 14.34 kg mL super(-1) respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds. |
| Author | Anjos, Ítalo C. Vasconcellos, Mário L.A.A. de Andrade, Natália G. Nerís, Patrícia L.N. Silva, Fábio P.L. Junior, Cláudio G.L. Carvalho, Gabriel A.U. Oliveira, Márcia R. de Assis, Priscila A.C. Segundo, Luiz V.G. Rocha, Gerd B. Barbosa, Ticiano P. Sousa, Suervy C.O. |
| Author_xml | – sequence: 1 givenname: Cláudio G.L. surname: Junior fullname: Junior, Cláudio G.L. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 2 givenname: Priscila A.C. surname: de Assis fullname: de Assis, Priscila A.C. organization: Departamento de Biologia Molecular, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 3 givenname: Fábio P.L. surname: Silva fullname: Silva, Fábio P.L. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 4 givenname: Suervy C.O. surname: Sousa fullname: Sousa, Suervy C.O. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 5 givenname: Natália G. surname: de Andrade fullname: de Andrade, Natália G. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 6 givenname: Ticiano P. surname: Barbosa fullname: Barbosa, Ticiano P. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 7 givenname: Patrícia L.N. surname: Nerís fullname: Nerís, Patrícia L.N. organization: Departamento de Biologia Molecular, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 8 givenname: Luiz V.G. surname: Segundo fullname: Segundo, Luiz V.G. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 9 givenname: Ítalo C. surname: Anjos fullname: Anjos, Ítalo C. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 10 givenname: Gabriel A.U. surname: Carvalho fullname: Carvalho, Gabriel A.U. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 11 givenname: Gerd B. surname: Rocha fullname: Rocha, Gerd B. organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 12 givenname: Márcia R. surname: Oliveira fullname: Oliveira, Márcia R. email: mrosa@dbm.ufpb.br organization: Departamento de Biologia Molecular, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil – sequence: 13 givenname: Mário L.A.A. surname: Vasconcellos fullname: Vasconcellos, Mário L.A.A. email: mlaav@quimica.ufpb.br organization: Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059-900, Brazil |
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| Keywords | Drugs Temperature effect Structure–activity-relationship Morita–Baylis–Hillman adducts Leishmania |
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| Snippet | We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on
L. Amazonensis and
L. chagasi and a... Sixteen aromatic Morita-Baylis-Hillman adducts (MBHA) 1-16 were efficiently synthesized in a one step Morita-Baylis-Hillman reaction (MBHR) involving... Sixteen aromatic Morita-Baylis-Hillman adducts (MBHA) 1- 16 were efficiently synthesized in a one step Morita-Baylis-Hillman reaction (MBHR) involving... |
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| SubjectTerms | Acrylates - chemistry Aldehydes - chemistry Antiparasitic Agents - chemical synthesis Antiparasitic Agents - chemistry Antiparasitic Agents - pharmacology Catalysis Drugs Green Chemistry Technology - economics Green Chemistry Technology - methods Humans Hydrocarbons, Aromatic - chemical synthesis Hydrocarbons, Aromatic - chemistry Hydrocarbons, Aromatic - pharmacology Leishmania Leishmania - drug effects Leishmania amazonensis Leishmania chagasi Leishmaniasis - drug therapy Morita–Baylis–Hillman adducts Piperazines - chemistry Structure–activity-relationship Temperature effect |
| Title | Efficient synthesis of 16 aromatic Morita–Baylis–Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi |
| URI | https://dx.doi.org/10.1016/j.bioorg.2010.08.002 https://www.ncbi.nlm.nih.gov/pubmed/20855101 https://search.proquest.com/docview/918041236 |
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