6-Oxyindan-1-ones with amino acid fragments
DOI:
https://doi.org/10.17721/fujcV6I2P18-26Keywords:
6-hydroxyindan-1-one, activated ester method, N-hydroxysuccinimide, amino acid derivativesAbstract
New indan-1-one derivatives (8 examples) with amino acid fragments were synthesized through the N-acylation of the amino acids by 2-(3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetic acid using the method of activated N-hydroxysuccinimide esters. To obtain corresponding methyl esters (2 examples) two ways were possible: the N-acylation of the amino acid methyl esters by 2-(3-oxo-2,3-dihydro-1-inden-5-yloxy)acetic acid through the activated imidazole derivatives or methylation of the carboxylic function of preformed N-{[(1-oxoindan-6-yl)oxy]acetyl}amino acids.
References
YOSHIHIRA K, FUKUOKA M, KUROYANAGI M, NATORI S, UMEDA M, MOROHOSHI T, ENOMOTO M, SAITO M. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. I. Introduction, extraction and fractionation of constituents, and toxicological studies including carcinogenicity tests.. CHEMICAL & PHARMACEUTICAL BULLETIN 1978;26(8):2346-2364. https://doi.org/10.1248/cpb.26.2346
Padwa A, Curtis EA, Sandanayaka VP, Weingarten MD. A New Synthetic Route to the Illudin and Pterosin Family of Sesquiterpenes. Paper presented at: Electronic Conference Trends Org. Chem., 1995 Jun 12 – Jul 7. The Royal Society of Chemistry: Cambridge, 1996. Keynote Paper 1. Available from: https://www.ch.ic.ac.uk/ectoc/papers/01/.
Canary J. Electronic Conference on Trends in Organic Chemistry: ECTOC-1/CD-ROM. June 12−July 7, 1995 Edited by Henry S. Rzepa, Christopher Leach, and Jonathan M. Goodman. The Royal Society of Chemistry: Cambridge, 1996. £50.00. ISBN 0-85404-8995.. Journal of the American Chemical Society 1997;119(19):4567-4567. https://doi.org/10.1021/ja9659232
Allegrini P, Mantegazza S, Razzetti G, inventor; Dipharma Francis S.r.l., assignee. A process for the preparation of delapril. European patent 1878740. 2008 Jan 16.
Birch AM, Bennett SNL, Campbell AD, Simpson I, Whittamore PRO, Whalley DP, Godfrey L, inventor; Astrazeneca AB, Astrazeneca UK Limited, assignee. Heterocyclic amide derivatives which possess glycogen phosphorylase inhibitory activity. WO2005/013981. 2005 Feb 17.
Tam, TF, Leung-Toung R, Wang Y, Zhao Y, Xin T, Li W, Wodzinska JM, Rabadia VS, Feeney CJ, inventor; Apotex Technologies Inc., assignee. Prodrugs of D-isoglutamyl-[D/L]-tryptophan. WO2012/129671. 2012 Oct 4.
Ingold C, Piggott H. CLXX.—The mobility of symmetrical triad systems. Part II. The conditions relating to systems terminated by the o-phenylene group. Derivatives of indene. J. Chem. Soc., Trans. 1923;123(0):1469-1509. https://doi.org/10.1039/ct9232301469
Turek M, Szczęsna D, Koprowski M, Bałczewski P. Synthesis of 1-indanones with a broad range of biological activity. Beilstein Journal of Organic Chemistry 2017;13:451-494. https://doi.org/10.3762/bjoc.13.48
Weinstock M, Bejar C, Wang R, Poltyrev T, Gross A, Finberg J, Youdim M. TV3326, a novel neuroprotective drug with cholinesterase and monoamine oxidase inhibitory activities for the treatment of Alzheimer’s disease. Advances in Research on Neurodegeneration 2000;:157-169. https://doi.org/10.1007/978-3-7091-6301-6_10
Zhu L, Hou Y, Shen X, Pan X, Zhang X, Yao X. Monoterpene pyridine alkaloids and phenolics from Scrophularia ningpoensis and their cardioprotective effect. Fitoterapia 2013;88:44-49. https://doi.org/10.1016/j.fitote.2013.04.005
Koelsch C, Scheiderbauer R. The Tautomerism of Indene1. Journal of the American Chemical Society 1943;65(12):2311-2314. https://doi.org/10.1021/ja01252a018
Bj⊘rnstad V, Undheim K. Cyclic Ketones in Spiroannulation. Synthetic Communications 2009;39(10):1793-1800. https://doi.org/10.1080/00397910802590936
Anderson G, Zimmerman J, Callahan F. N-Hydroxysuccinimide Esters in Peptide Synthesis. Journal of the American Chemical Society 1963;85(19):3039-3039. https://doi.org/10.1021/ja00902a047
Gershkovich AA, Kibirev VK. Chemical Synthesis of Peptides [in Russian]. Kyiv: Naukova Dumka; 1992, pp. 38-44.
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