DOI: https://doi.org/10.18524/2304-0947.2017.4(64).115919

НОВИЙ МЕТОД ОТРИМАННЯ 6-НІТРО-2-(4-ВОС-ПІПЕРАЗИН- 1-ІЛ)-3H-ХІНАЗОЛІН-4-ОНУ

A. Yu. Kornylov, A. A. Krysko, O. L. Krysko, S. E. Sambursky, S. A. Andronati

Анотація


Запропоновано ефективний метод синтезу, що каталізується паладієм, 6-нітро-2-(4-Вос-піперазин-1-іл)-3H-хіназолін-4-ону. Використання предкаталізатора третього покоління XantPhos-Pd-G3 призводить до отримання цільового продукту з більшим виходом, в порівнянні з застосуванням каталітичної системи Pd2(dba)3. СHСl3-Xantphos. Цей спосіб має потенційне значення для конструювання різних 2-аміно-3H-хіназолін-4-онів.

Ключові слова


2-аміно-3Н-хіназолін-4-они, паладієвий каталіз, C-N кросстикування

Повний текст:

PDF (Русский)

Посилання


Pendergast W., Johnson J.V., Dickerson S.H., Dev I.K., Duch D.S., Ferone R., Hall W.R., Humphreys J.,Kelly J.M., Wilson D.C. Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones. J. Med. Chem., 1993, vol. 36, no 16, pp. 2279-2291. https://doi.org/10.1021/jm00068a004

Chern J.-W., Tao P.-L, Wang K.-C., Gutcait A., Liu S.-W., Yen M.-H., Chien S.-L., Rong J.-K. Studies on Quinazolines and 1,2,4-Benzothiadiazine 1,1-Dioxides. 8. Synthesis and Pharmacological Evaluation of Tricyclic Fused Quinazolines and 1,2,4-Benzothiadiazine 1,1-Dioxides as Potential α1-Adrenoceptor Antagonists. J. Med. Chem., 1998, vol. 41, no 17, pp. 3128-3141. https://doi.org/10.1021/jm970159v

Grosso J.A., Nichols D.E., Kohli J.D., Glock D. Synthesis of 2-(alkylamino)-5,6- and -6,7-dihydroxy-3,4-dihydroquinazolines and evaluation as potential dopamine agonists. J. Med. Chem., 1982, vol. 25, no 6, pp.703-708. https://doi.org/10.1021/jm00348a018

Alagarsamy V., Dhanabal K., Parthiban P., Anjana G., Deepa G., Murugesan B., Rajkumar S., Beevi A.J. Synthesis and pharmacological investigation of novel 3-(3-methylphenyl)-2-substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents. J. Pharm. Pharmacol., 2007, vol. 59, no 5, pp. 669-677. https://doi.org/10.1211/jpp.59.5.0007

Levin J.I., Fanshawe W.J., Epstein J.W., Beer B., Bartus R.T., Dean R.L. Synthesis and activity in cognitionrelated tests of novel 2-benzoylamino-4-oxoquinazolines. Bioorg. Med. Chem. Lett., 1992, vol. 2, no 4, pp.349-352. https://doi.org/10.1016/S0960-894X(01)80217-1

Smits R.A., de Esch I.J.P., Zuiderveld O.P., Broeker J., Sansuk K., Guaita E., Coruzzi G., Adami M., Haaksma E., Leurs R. Discovery of Quinazolines as Histamine H4 Receptor Inverse Agonists Using a Scaffold Hopping Approach. J. Med. Chem., 2008, vol. 51, no 24, pp. 7855-7865. https://doi.org/10.1021/jm800876b

Polishchuk P.G., Samoylenko G.V., Khristova T.M., Krysko O.L., Kabanova T.A., Kabanov V.M., Kornylov A.Yu., Klimchuk O., Langer T., Andronati S.A., Kuz’min V.E., Krysko A.A., Varnek A. Design, Virtual Screening, and Synthesis of Antagonists of αIIbβ3 as Antiplatelet Agents. J. Med. Chem., 2015, vol. 58, no 19, pp. 7681-7694. https://doi.org/10.1021/acs.jmedchem.5b0086

Krysko A.A., Kornylov A.Yu., Polishchuk P.G., Samoylenko G.V., Krysko O.L., Kabanova T.A., Kravtsov V. Ch., Kabanov V.M., Wicher B., Andronati S.A. Synthesis, biological evaluation and molecular docking studies of 2-piperazin-1-yl-quinazolines as platelet aggregation inhibitors and ligands of integrin αIIbβ3. Bioorg. Med. Chem. Lett., 2016, vol. 26, no 7, pp. 1839-1843. https://doi.org/10.1016/j.bmcl.2016.02.011

Hartwig J.F. Palladium-Catalyzed Amination of Aryl Halides and Related Reactions. Handbook of Organopalladium Chemistry for Organic Synthesis. Vol. 1. Ed. by. Ei-ichi Negishi. Wiley-Interscience, New York, 2002, pp. 1051-1097. https://doi.org/10.1002/0471212466.ch42

Muci A.R., Buchwald S.L. Practical Palladium Catalysts for C-N and C-O Bond Formation. Top. Curr. Chem., 2002, vol. 219, pp. 131-209.https://doi.org/10.1007/3-540-45313-X_5

Prim D., Campagne J.-M., Joseph D., Andrioletti B. Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles. Tetrahedron, 2002, vol. 58, no 11, pp. 2041-2075. https://doi.org/10.1016/ S0040-4020(02)00076-5

Willis M.C., Snell R.H., Fletcher A.J., Woodward R.L. Tandem Palladium-Catalyzed Urea Arylation- Intramolecular Ester Amidation: Regioselective Synthesis of 3-Alkylated 2,4-Quinazolinediones. Org. Lett., 2006, vol. 8, no 22, pp. 5089-5091. https://doi.org/10.1021/ol062009x

Li B., Samp L., Sagal J., Hayward C.M., Yang C., Zhang Z. Synthesis of Quinazolin-4(3H)-ones via Amidine N-Arylation. J. Org. Chem., 2013, vol. 78, no 3, pp. 1273-1277. https://doi.org/10.1021/jo302515c

Wu M.T., MacCoss M., Ikeler T.J., Hirshfield J., Arison B.H., Tolman R.L. Annelated piperazinyl-7,8-dihydro- 6H-thiopyrano[3,2-d]pyrimidines. J. Heterocycl. Chem., 1990, vol. 27, no 6, pp. 1559-1563. https://doi. org/10.1002/jhet.5570270607

Short J.H., Biermacher U., Dunnigan D.A., Leth T.D. Sympathetic Nervous System Blocking Agents. Derivatives of Guanidine and Related Compounds. J. Med. Chem., 1963, vol. 6, no 3, pp. 275-283. https://doi.org/10.1021/ jm00339a013

Zalesskiy S.S., Ananikov V.P. Pd2(dba)3 as a Precursor of Soluble Metal Complexes and Nanoparticles: Determination of Palladium Active Species for Catalysis and Synthesis. Organometallics., 2012, vol. 31, no 6, pp. 2302-2309. https://doi.org/10.1021/om201217r

Bruno N.C., Tudge M.T., Buchwald S.L. Design and preparation of new palladium precatalysts for C–C and C–N cross-coupling reactions. Chem. Sci., 2013, vol. 4, no 3, pp. 916-920. https://doi.org/10.1039/C2SC20903A


Пристатейна бібліографія ГОСТ


1. Pendergast W., Johnson J.V., Dickerson S.H., Dev I.K., Duch D.S., Ferone R., Hall W.R., Humphreys J.,Kelly J.M., Wilson D.C. Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones // J. Med. Chem. – 1993. – Vol. 36, N 16. – P. 2279-2291. https://doi.org/10.1021/jm00068a004

2. Chern J.-W., Tao P.-L, Wang K.-C., Gutcait A., Liu S.-W., Yen M.-H., Chien S.-L., Rong J.-K. Studies on Quinazolines and 1,2,4-Benzothiadiazine 1,1-Dioxides. 8. Synthesis and Pharmacological Evaluation of Tricyclic Fused Quinazolines and 1,2,4-Benzothiadiazine 1,1-Dioxides as Potential α1-Adrenoceptor Antagonists // J. Med. Chem. – 1998. – Vol. 41, N 17. – P. 3128-3141. https://doi.org/10.1021/jm970159v

3. Grosso J.A., Nichols D.E., Kohli J.D., Glock D. Synthesis of 2-(alkylamino)-5,6- and -6,7-dihydroxy-3,4- dihydroquinazolines and evaluation as potential dopamine agonists // J. Med. Chem. – 1982. – Vol. 25, N 6. – P. 703-708. https://doi.org/10.1021/jm00348a018

4. Alagarsamy V., Dhanabal K., Parthiban P., Anjana G., Deepa G., Murugesan B., Rajkumar S., Beevi A.J. Synthesis and pharmacological investigation of novel 3-(3-methylphenyl)-2-substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents // J. Pharm. Pharmacol. – 2007. – Vol. 59, N 5. – P. 669-677.https://doi.org/10.1211/jpp.59.5.0007

5. Levin J.I., Fanshawe W.J., Epstein J.W., Beer B., Bartus R.T., Dean R.L. Synthesis and activity in cognitionrelated tests of novel 2-benzoylamino-4-oxoquinazolines // Bioorg. Med. Chem. Lett. – 1992. –Vol. 2, N 4. – P. 349-352. https://doi.org/10.1016/S0960-894X(01)80217-1

6. Smits R.A., de Esch I.J.P., Zuiderveld O.P., Broeker J., Sansuk K., Guaita E., Coruzzi G., Adami M., Haaksma E., Leurs R. Discovery of Quinazolines as Histamine H4 Receptor Inverse Agonists Using a Scaffold Hopping Approach // J. Med. Chem. – 2008. – Vol. 51, N 24. – P. 7855-7865. https://doi.org/10.1021/jm800876b

7. Polishchuk P.G., Samoylenko G.V., Khristova T.M., Krysko O.L., Kabanova T.A., Kabanov V.M., Kornylov A.Yu., Klimchuk O., Langer T., Andronati S.A., Kuz’min V.E., Krysko A.A., Varnek A. Design, Virtual Screening, and Synthesis of Antagonists of αIIbβ3 as Antiplatelet Agents // J. Med. Chem. – 2015. – Vol. 58, N 19. – P. 7681-7694. https://doi.org/10.1021/acs.jmedchem.5b0086

8. Krysko A.A., Kornylov A.Yu., Polishchuk P.G., Samoylenko G.V., Krysko O.L., Kabanova T.A., Kravtsov V.Ch., Kabanov V.M., Wicher B., Andronati S.A. Synthesis, biological evaluation and molecular docking studies of 2-piperazin-1-yl-quinazolines as platelet aggregation inhibitors and ligands of integrin αIIbβ3 // Bioorg. Med. Chem. Lett. – 2016. –Vol. 26, N 7. – P. 1839-1843. https://doi.org/10.1016/j.bmcl.2016.02.011

9. Hartwig J.F. Palladium-Catalyzed Amination of Aryl Halides and Related Reactions / Handbook of Organopalladium Chemistry for Organic Synthesis. Vol. 1. Ed. by. Ei-ichi Negishi // Wiley-Interscience: New York – 2002. – P. 1051-1097. https://doi.org/10.1002/0471212466.ch42

10. Muci A.R., Buchwald S.L. Practical Palladium Catalysts for C-N and C-O Bond Formation // Top. Curr. Chem. – 2002. – Vol. 219. – P. 131-209. https://doi.org/10.1007/3-540-45313-X_5

11. Prim D., Campagne J.-M., Joseph D., Andrioletti B. Palladium-catalysed reactions of aryl halides with soft, nonorganometallic nucleophiles // Tetrahedron – 2002. – Vol. 58, N11. – P. 2041-2075. https://doi.org/10.1016/S0040-4020(02)00076-5

12. Willis M.C., Snell R.H., Fletcher A.J., Woodward R.L. Tandem Palladium-Catalyzed Urea Arylation-Intramolecular Ester Amidation: Regioselective Synthesis of 3-Alkylated 2,4-Quinazolinediones // Org. Lett. –2006. – Vol. 8, N 22. – P. 5089-5091. https://doi.org/10.1021/ol062009x

13. Li B., Samp L., Sagal J., Hayward C.M., Yang C., Zhang Z. Synthesis of Quinazolin-4(3H)-ones via Amidine N-Arylation //J. Org. Chem. – 2013. – Vol. 78, N 3. – P. 1273-1277. https://doi.org/10.1021/jo302515c

14. Wu M.T., MacCoss M., Ikeler T.J., Hirshfield J., Arison B.H., Tolman R.L. Annelated piperazinyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidines // J. Heterocycl. Chem. – 1990. – Vol. 27, N 6. – P. 1559-1563. https://doi. org/10.1002/jhet.5570270607

15. Short J.H., Biermacher U., Dunnigan D.A., Leth T.D. Sympathetic Nervous System Blocking Agents. Derivatives of Guanidine and Related Compounds // J. Med. Chem. – 1963. – Vol. 6, N 3. – P. 275-283. https://doi.org/10.1021/jm00339a013

16. Zalesskiy S.S., Ananikov V.P. Pd2(dba)3 as a Precursor of Soluble Metal Complexes and Nanoparticles: Determination of Palladium Active Species for Catalysis and Synthesis // Organometallics. – 2012. – Vol. 31, N 6. – P. 2302-2309. https://doi.org/10.1021/om201217r

17. Bruno N.C., Tudge M.T., Buchwald S.L. Design and preparation of new palladium precatalysts for C–C and C–N cross-coupling reactions// Chem. Sci. – 2013. – Vol. 4, N 3. – P. 916-920. https://doi.org/10.1039/C2SC20903A





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