Synthesis of Macrolides with Fragments of Diethylene Glycol and Hydrazides of Dicarboxylic Acids from 7-Oxooctanoic Acid
DOI: 10.6060/mhc224242y
Аннотация
Исходя из доступной 7-оксооктановой кислоты разработаны синтезы двух потенциально полезных макролидов с диэтиленгликольным и дигидразидными фрагментами с использованием на ключевых стадиях [2+1]-взаимодействия последней с дитозилатом диэтиленгликоля и [1+1]-конденсации образующегося α,ω-дикетодиэфира с дигидразидами адипиновой и L-(+)-винной кислот. Структура полученных соединений установлена с помощью ИК- и ЯМР-спектроскопии и подтверждена данными хромато-масс-спектрометрии.
Литература
Ishmuratov G.Y., Yakovleva M.P., Botsman L.P., Ishmuratova N.M., Muslukhov R.R., Khambalova G.V., Tolstikov G.A. Chem. Nat. Compd. 2003, 39, 28-30. https://doi.org/10.1023/A:1024172327822
Ishmuratov G.Y., Yakovleva M.P., Zaripova G.V., Botsman L.P., Ishmuratova N.M. Bashkir Khim. Zh. [Bashkir Сhemistry Journal] 2004, 11, 36-38.
Preparation of positively charged non-natural amino acids for the synthesis of peptides. PCT Int. Appl. Patent 9817626 (publ. 1998).
Biswas S., Maiti S., Jana U. Eur. J. Org. Chem. 2010, 2010, 2861-2866. https://doi.org/10.1002/ejoc.201000128
Kawata A., Takata K., Kuninobu Y., Takai K. Angew. Chem. Int. Ed. 2007, 46, 7793-7795. https://doi.org/10.1002/anie.200702798
Yamashita T., Matsushita S., Nagatomo T., Yamauchi R. Res. Chem. Intermed. 2013, 39, 111-126. https://doi.org/10.1007/s11164-012-0636-4
Isaeva Z.G., Karaseva A.N., Karlin V.V., Savukhina L.A. Russ. Chem. Bull. 1986, 2134-2136.
Jaeger R.H., Robinson R. Tetrahedron 1961, 14, 320-321. https://doi.org/10.1016/S0040-4020(01)92182-9
Ebert G.W. Synth. Commun. 1991, 21, 1527-1533. https://doi.org/10.1080/00397919108016427
Gao Z.-L. Yingyong Huaxue 2001, 18, 589-591. https://doi.org/10.1093/oq/18.4.589
Kancharla P., Lu W., Salem S.M., Kelly J.X., Reynolds K.A. J. Org. Chem. 2014, 79, 11674-11689. https://doi.org/10.1021/jo5023553
Preparation of 2-acylamino-3-morpholino-1-phenylpropanols as neuroprotectants. Eur. Pat. 1106609 B1 (publ. 2001).
Walter M.A., Pfeifer D., Kraus W., Emmerling F., Schneider R.J., Panne U., Weller M.G. Langmuir 2010, 26, 15418-15423. https://doi.org/10.1021/la1018339
Preparation of 2-(N-Substitutedpiperazinyl)steroid Derivatives as Anticancer Agents. PCT Int. Appl. Pat. 2010060215 (publ. 2010).
Kolasa T., Gunn D.E., Bhatia P., Woods K.W., Gane T., Stewart A.O., Bouska J.B., Harris R.R., Hulkower K.I., Malo P.E., Bell R.L., Carter G.W., Brooks C.D.W. J. Med. Chem. 2000, 43, 690-705. https://doi.org/10.1021/jm9904102
Reitz A.B., Sonveaux E., Rosenkranz R.P., Verlander M.S., Melmon K.L., Hoffman B.B., Akita Y., Castagnoli N., Goodman M. J. Med. Chem. 1985, 28, 634-642. https://doi.org/10.1021/jm50001a017
Preparation of Compounds and Lipid Nanoparticle Compositions for Intracellular Delivery of Therapeutic Agents. PCT Int. Appl. Pat. 2017049245 (publ. 2017).
Preparation of Nitrogen-Containing Compounds or Their Metal Complexes as Therapeutic and Radiodiagnostic Agents for Integrin-related Disorders. PCT Int. Appl. Pat, 2015046278 (publ. 2015).
Umezawa K., Citterio D., Suzuki K. Anal. Sci. 2008, 24, 213-217. https://doi.org/10.2116/analsci.24.213
Torisu K., Kobayashi K., Iwahashi M., Egashira H., Nakai Y., Okada Y., Nanbu F., Ohuchida S., Nakai H., Toda M. Eur. J. Med. Chem. 2005, 40, 505-519. https://doi.org/10.1016/j.ejmech.2004.11.011
Harriman G.C.B. Tetrahedron Lett. 1997, 38, 5591-5594. https://doi.org/10.1016/S0040-4039(97)01265-3
Stille J.K., Tanaka M. J. Am. Chem. Soc. 1987, 109, 3785-3786. https://doi.org/10.1021/ja00246a048
Yoshida M., Harada N., Nakamura H., Kanematsu K. Tetrahedron Lett. 1988, 29, 6129-6132. https://doi.org/10.1016/S0040-4039(00)82285-6
Gordon A.J., Ford R.A. The Chemist's Companion: A Handbook of Practical Data, Techniques, and References (Russ. transl.). Мoscow: Mir, 1976. 541 p.
Weygand-Hilgetag. Organisch-chemische Experimentierkunst (Russ. transl.). Мoscow: Khimiya, 1968. 944 p.
Neudachina L.K., Petrova Yu.S. Application of Macrocyclic Compounds in Analysis: Study Guide (Petrova Yu.S., Ed.), Ekaterinburg: Ural State University, 2018. 118 p.
Khiati Z., Cherchar A., Othman A.A. Chem. Sci. Trans. 2012, 1, 185-193.
Chen Z., Zhou S., Shen Y., Zou H., Liu D., Liang F. Eur. J. Inorg. Chem. 2014, 2014, 5783-5792. https://doi.org/10.1002/ejic.201402784
Nour H.F., Hourani N., Kuhnert N. Org. Biomol. Chem. 2012, 10, 4381-4389. https://doi.org/10.1039/c2ob25171j