6-Oxyindan-1-ones with dipeptide chains

Authors

  • Serhiy Shilin
  • Olga Shablykina
  • Igor Levkov
  • Oleksandra Bugera
  • Zoia Voitenko

DOI:

https://doi.org/10.17721/fujcV7I2P111-119

Keywords:

6-hydroxyindan-1-one, dipeptide derivatives, oxyacetic linker, activated ester method, N-hydroxysuccinimide

Abstract

Through N-acylation of a- or b-amino acid units by 2-(3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetic acid using the method of N-hydroxysuccinimide esters new dipeptide indan-1-one derivatives were obtained. In general, the direct interaction of the acetic carboxyl group of the substrate with the amino group of the a- or b-dipeptide is a more productive strategy than the sequential peptidic condensation of the two amino acids.

References

KUROYANAGI M, FUKUOKA M, YOSHIHIRA K, NATORI S. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. III. Further characterization of pterosins and pterosides, sesquiterpenes and the glucosides having 1-indanone skeleton, from the rhizomes.. CHEMICAL & PHARMACEUTICAL BULLETIN 1979;27(3):592-601. https://doi.org/10.1248/cpb.27.592

Finkielsztein L, Alesso E, Lantaño B, Aguirre J, Moltrasio Iglesias G, . A Simple Synthetic Route to Pterosin F and Other Pterosins. Journal of Chemical Research 1999;(6):406-406. https://doi.org/10.1039/a900445i

Hsu F, Huang C, Chen Y, Yen Y, Wu C, Uang B, Yang R, Liu S. Antidiabetic Effects of Pterosin A, a Small-Molecular-Weight Natural Product, on Diabetic Mouse Models. Diabetes 2012;62(2):628-638. https://doi.org/10.2337/db12-0585

Yahara Y, Takemori H, Okada M, Kosai A, Yamashita A, Kobayashi T, Fujita K, Itoh Y, Nakamura M, Fuchino H, Kawahara N, Fukui N, Watanabe A, Kimura T, Tsumaki N. Pterosin B prevents chondrocyte hypertrophy and osteoarthritis in mice by inhibiting Sik3. Nature Communications 2016;7(1):10959. https://doi.org/10.1038/ncomms10959

Bycroft B. Dictionary of Antibiotics and Related Substances. CRC Press; 2013, p. 1006. https://doi.org/10.1201/9781482282153

Okpekon T, Millot M, Champy P, Gleye C, Yolou S, Bories C, Loiseau P, Laurens A, Hocquemiller R. A novel 1-indanone isolated fromUvaria afzeliiroots. Natural Product Research 2009;23(10):909-915. https://doi.org/10.1080/14786410802497240

Rukachaisirikul V, Buadam S, Sukpondma Y, Phongpaichit S, Sakayaroj J, Hutadilok-Towatana N. Indanone and mellein derivatives from the Garcinia-derived fungus Xylaria sp. PSU-G12. Phytochemistry Letters 2013;6(1):135-138. https://doi.org/10.1016/j.phytol.2012.11.007

Nagle D, Zhou Y, Park P, Paul V, Rajbhandari I, Duncan C, Pasco D. A New Indanone from the Marine CyanobacteriumLyngbya majusculaThat Inhibits Hypoxia-Induced Activation of the VEGF Promoter in Hep3B Cells. Journal of Natural Products 2000;63(10):1431-1433. https://doi.org/10.1021/np000216e

Ahmed N. Synthetic Advances in the Indane Natural Product Scaffolds as Drug Candidates. Studies in Natural Products Chemistry 2016;:383-434. https://doi.org/10.1016/b978-0-444-63932-5.00008-5

Patel VK, Dhrubo JS, Patel CN. Anti-microbial and antifungal screening of indanone acetic acid derivatives. J. Chem. Pharm. Res. 2010; 2(2): 50-56. http://www.jocpr.com/abstract/antimicrobial-and-antifungal-screening-of-indanone-acetic-acid-derivatives-78.html

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

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.

Shilin S, Lenko I, Shablykina O, Khilya V. 6-Oxyindan-1-ones with amino acid fragments. French-Ukrainian Journal of Chemistry 2018;6(2):18-26. https://doi.org/10.17721/fujcv6i2p18-26

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

Downloads

Published

2019-12-24

Issue

Vol. 7 No. 2 (2019)

Section

Articles

License

Authors who publish with this journal agree to the following terms:

  • Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

  • Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.

  • Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).