Synthesis of Aromatic Amides and Isoquinolines Based on Homoveratrilamine
Keywords:
Homoveratrylamine, cinnamic acid, mandelic acid, amide, 3,4-dihydroisoquinoline, tetrahydroisoquinoline, cyclization, Bischler-Napieralski, NMR spectroscopy, mass spectrometry.
Abstract
This paper outlines the synthesis of aromatic amides and isoquinoline derivatives derived from homoveratrylamine. Condensation reactions of homoveratrylamine with cinnamic and mandelic acids gave the corresponding amides in high yields. The cyclization of these amides via the Bischler-Napieralski method facilitated the synthesis of 3,4-dihydro- and tetrahydroisoquinoline derivatives. The synthesized compounds were confirmed through IR and NMR spectroscopy, as well as mass spectrometry. The results highlight the potential of these methods for synthesizing biologically active compounds based on homoveratrylamine.
References
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[11] Саидов А.Ш., Тургунов К.К., Ташходжаев Б., Виноградова В.И. Синтез 6,7-диметокси-1,3,4,8b-тетрагидроазирино [2,1-a] изохинолин-n-борана и бис-(6,7-диметокси-1,2,3,4-тетрагидро-изохинолин)-1,1′-ена // Химия природных соединений.-2014.- №5.- C. 771-774.
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[13] Saidov, A. S., Levkovich, M. G., Alimova, M., & Vinogradova, V. I. Synthesis of bis-Tetrahydroisoquinolines Based on Homoveratrylamine and Dibasic Acids. 2. Chemistry of natural compounds, (2014). 49(6), 1099-1104.
[2] Bendale, Atul R., et al. "Development and characterization of novel amino acid conjugates of aceclofenac." Int. J. Pharm. Tech. Res. – 2011. – Т. 3. – №. 2. – С. 841–851.
[3] Y Dutha Reddy,Y Bharathi Kumari, P K.Dubey, synthesis of a novel water soluble phthalimide derivative of acetaminophen as potential analgesic and antipyretic agent, Indian Journal of chemistry. 2013,52B, ,691-693.
[4] Saidov, A. S., Turgunov, K. K., Levkovich, M. G., & Vinogradova, V. I. Synthesis of bis-tetrahydroisoquinolines based on homoveratrylamine and several dibasic acids. 4. Reaction with malonic and succinic acids. Chemistry of Natural Compounds, (2015). 51(2), 316-319.
[5] Larghi, E. L., Bohn, M. L., & Kaufman, T. S. Aaptamine and related products. Their isolation, chemical syntheses, and biological activity. Tetrahedron, 2009. 65(22), 4257-4282.
[6] Qing, Z. X., Huang, J. L., Yang, X. Y., Liu, J. H., Cao, H. L., Xiang, F., ... & Zeng, J. G. (2018). Anticancer and reversing multidrug resistance activities of natural isoquinoline alkaloids and their structure-activity relationship. Current medicinal chemistry, 25(38), 5088-5114.
[7] Терентьева Е.О., Хашимова З.С., Цеомашко Н.Е., Саидов А.Ш., Виноградова В.И., Азимова Ш.С. Цитотоксическая активность бис-тетрагидроизохинолинов// Журнал теоретической и клинической медицины, 2015. - №5. – С.20-23.
[8] Ericsson David Coy Barrera, Luıs Enrique Cuca Suarez, Biochemical Systematics and Ecology, 36, 674 (2008); Silvia Sepulveda-Boza, Sualaheen Delhvi, Bruce K. Cassels, Phytochemistry, 29, 2357 (1990)
[9] Usifoh C. O. et al. Synthesis and anticonvulsant activity of N, N‐phthaloyl derivatives of central nervous system inhibitory amino acids //Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry. – 2001. – Т. 334. – №. 10. – С. 323–331.
[10] Diaz, G., Miranda, I. L., & Diaz, M. A. N. Quinolines, isoquinolines, angustureine, and congeneric alkaloids—occurrence, chemistry, and biological activity. Phytochemicals-isolation, characterisation and role in human health, 2015, 141-162.
[11] Саидов А.Ш., Тургунов К.К., Ташходжаев Б., Виноградова В.И. Синтез 6,7-диметокси-1,3,4,8b-тетрагидроазирино [2,1-a] изохинолин-n-борана и бис-(6,7-диметокси-1,2,3,4-тетрагидро-изохинолин)-1,1′-ена // Химия природных соединений.-2014.- №5.- C. 771-774.
[12] Саидов А.Ш., Виноградова В.И. Синтез тетрагидроизохинолинов на основе гомовератриламина и пиридиновых кислот // Узбекский химический журнал.- 2014.- №2.- C. 16-19
[13] Saidov, A. S., Levkovich, M. G., Alimova, M., & Vinogradova, V. I. Synthesis of bis-Tetrahydroisoquinolines Based on Homoveratrylamine and Dibasic Acids. 2. Chemistry of natural compounds, (2014). 49(6), 1099-1104.
Published
2024-10-10
How to Cite
Urunbaeva Ziroat Erkinovna, Saidov Abdusalom Shomurodovich, & Vinogradova Valentina Ivanovna. (2024). Synthesis of Aromatic Amides and Isoquinolines Based on Homoveratrilamine. Central Asian Journal of Medical and Natural Science, 5(4), 935-939. Retrieved from https://cajmns.centralasianstudies.org/index.php/CAJMNS/article/view/2636
Section
Articles
