التفاصيل البيبلوغرافية
| العنوان: |
Synthesis of A-ring quinolones, nine-membered oxolactams and spiroindoles by oxidative transformations of 2,3-indolotriterpenoids. |
| المؤلفون: |
Khusnutdinova EF; Ufa Institute of Chemistry - Subdivision of the Ufa Federal Research Centre of Russian Academy of Sciences, Ufa 450054, Russian Federation. obf@anrb.ru., Kazakova OB, Lobov AN, Kukovinets OS, Suponitsky KY, Meyers CB, Prichard MN |
| المصدر: |
Organic & biomolecular chemistry [Org Biomol Chem] 2019 Jan 16; Vol. 17 (3), pp. 585-597. |
| نوع المنشور: |
Journal Article |
| اللغة: |
English |
| بيانات الدورية: |
Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Print Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: PubMed not MEDLINE |
| أسماء مطبوعة: |
Original Publication: Cambridge, UK : Royal Society of Chemistry, c2003- |
| مستخلص: |
This paper describes an access to new nitrogen-containing heterocyclic triterpenoids by the reaction of 2,3-indolotriterpenoids with ozone and dimethyldioxirane. The oxidation of indolo-fused 28-oxo-allobetulin or methyl platanoate with ozone led to a mixture of a quinolone as the major product and a nine-membered 2,3-seco-2-oxolactam and three different types of spiroindoles as byproducts. The formation of quinolone and 2,3-seco-2-oxolactam derivatives could be explained by the standard 1,3-dipolar cycloaddition of ozone to the C2(3)-double bond of the triterpene core similar to the products observed in the ozonolysis of indoles in the Witkop-Winterfeldt oxidation (WWO). The formation of spiroindoles was unexpected and could be explained through the 1,2-cycloaddition of ozone to the C2(3)-double bond with consecutive intramolecular rearrangements of the 2,3-epoxy-intermediate. These spiroindoles seem to be novel structures observed in the WWO reaction. The formation of only two isomeric triterpene spiroindolinones was achieved by the oxidation of 2,3-indolo-28-oxo-allobetulin with dimethyldioxirane that could be explained by the rearrangement of the 2,3-epoxy-intermediate. 19β,28-Epoxy-18α-olean-28-oxo-2-nor-2,3-4'(1H)-quinolone was the most active against HPV-11 with EC50 0.45 μM and SI50 322 in a primary assay and SI90 < 10 against HPV-16 in a secondary assay. The oxidative transformations of indolotriterpenoids have great potential for further modifications towards the preparation of new biologically active compounds. |
| تواريخ الأحداث: |
Date Created: 20181222 Date Completed: 20190204 Latest Revision: 20230106 |
| رمز التحديث: |
20231215 |
| DOI: |
10.1039/c8ob02624f |
| PMID: |
30574983 |
| قاعدة البيانات: |
MEDLINE |
