Synthesis of new lamivudine, adamantine and warfarin derivatives from isoxazole carboxylic acids and their esters as compounds with possible antiviral activity

被引:0
|
作者
Michalski, Aleksander [1 ,2 ]
Maranda, Andrzej [3 ]
Kwiatek, Magdalena [2 ]
Gucma, Miroslaw [3 ]
Michalczyk, Alicja [3 ]
机构
[1] Wojskowy Szpital Kliniczny Poliklin, SP ZOZ Lublinie, Lublinie, Poland
[2] Wojskowy Inst Higieny Epidemiol, Pulawy, Poland
[3] Siec Badawcza Lukasiewicz Inst Przemyslu Organ, Warsaw, Poland
来源
PRZEMYSL CHEMICZNY | 2023年 / 102卷 / 04期
关键词
antivirals; protease activity; lamivudine; warfarin; adamantine; isoxazoles; 1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDES; BIOLUMINESCENCE; ISOXAZOLECARBOXAMIDES;
D O I
10.15199/62.2023.4.5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Fifteen new lamivudine, warfarin and adamantine derivatives were synthesized and identified by NMR spectroscopy. In particular, 3-cykloheksyl-2-isoxazolin-5-carboxyl acid and its Et ester, adamantine amides and lamivudine amides of 3-phenyl-2-isoxazolin-5- carboxylic, 3-(4- trifluormethyl-phenyl)- 2- isoxazolin5- carboxylic, 3-( 4-trifluormethyl-phenyl)-2- isoxazol-5- carboxylic, 3-(3-trifluormethyl- phenyl)-2- isoxazolin-5-carboxylic acid, 3-(2,4,5- trifluorphenyl)-2-isoxazolin-5-carboxylic, 3-(tert-butyl)2-isoxazolin- 5-carboxylic and 3-(cyclohexyl)-2-isoxazolin- 5-carboxylic acids as well as warfarinic esters of 3-(phenyl)-2-isoxazolin-5-carboxylic and 3-( cyclohexyl)-2-isoxazolin-5-carboxylic acids were prepd. Adamantine- derived amides were prepd. from all the acids. The compds. should have antiviral and anti- inflammatory activities as well as should show an inhibitory effect on tumors. Quantities necessary for basic antiviral tests for indicative activities against a representative of the pathogenic virus from each group were synthesized.
引用
收藏
页码:368 / 375
页数:8
相关论文
共 50 条
  • [31] DERIVATIVES OF IMIDAZOLE DICARBOXYLIC ACIDS .3. SYNTHESIS OF 2-PYRIDYL THIAZOLIDINES AND 4-CARBOXYLIC ACIDS AND 2-METHYL COMPOUNDS DERIVED FROM THEM
    VINOGRAD.NB
    KHROMOVBORISOV, NV
    ZHURNAL OBSHCHEI KHIMII, 1961, 31 (05): : 1483 - &
  • [32] SYNTHESIS OF ESTERS AND OTHER DERIVATIVES OF CARBOXYLIC ACIDS FROM CARBON MONOXIDE, OLEFINS, AND ACYLATING COMPOUNDS UNDER ACID CATALYSIS CONDITIONS .5. SYNTHESIS OF ESTERS OF CIS-DECALIN-9-CARBOXYLIC ACID FROM CYCLOPENTENE AND 4,7-ENDOMETHYLENEHYDRINDANCARBOXYLIC ACID FROM 4, 5, 6, 7, 8, 9,-HEXAHYDRO-4,7-ENDOMETHYLENEINDENE
    EIDUS, YT
    GUSEVA, IV
    PUZITSKII, KV
    JOURNAL OF GENERAL CHEMISTRY USSR, 1961, 31 (04): : 1227 - &
  • [33] STUDIES ON ORGANO-PHOSPHORUS COMPOUNDS .48. SYNTHESIS OF DITHIOESTERS FROM P,S-CONTAINING REAGENTS AND CARBOXYLIC-ACIDS AND THEIR DERIVATIVES
    YOUSIF, NM
    PEDERSEN, U
    YDE, B
    LAWESSON, SO
    TETRAHEDRON, 1984, 40 (14) : 2663 - 2669
  • [34] Synthesis and Antimicrobial Activity of New 1,3-Thiazolidin-4-one Derivatives Obtained from Carboxylic Acid Hydrazides
    Popiolek, Lukasz
    Biernasiuk, Anna
    Malm, Anna
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (02) : 251 - 260
  • [35] Quinolone nucleosides:: 6,7-dihalo-N-β- and α-glycosyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acids and derivatives.: Synthesis, antimicrobial and antiviral activity
    Al-Masoudi, NA
    Al-Soud, YA
    Ehrmann, M
    de Clercq, E
    NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (12): : 2255 - 2266
  • [36] SYNTHESIS OF ESTERS AND OTHER DERIVATIVES OF CARBOXYLIC ACIDS UNDER CONDITIONS OF ACIDIC CATALYSIS FROM CARBON MONOXIDE OLEFINS AND ACYLATING COMPOUNDS .12. INFLUENCE OF CONDITIONS ON METHOXYCARBONYLATION OF PENTAN-1-OL ISOBUTYLENE AND A MIXTURE OF NORMAL BUTENES
    EIDUS, YT
    KAAL, TA
    JOURNAL OF GENERAL CHEMISTRY USSR, 1964, 34 (11): : 3747 - &
  • [37] New Dihydroxytyrosyl Esters from Dicarboxylic Acids: Synthesis and Evaluation of the Antioxidant Activity In Vitro (ABTS) and in Cell-Cultures (DCF Assay)
    Roma, Elia
    Mattoni, Elena
    Lupattelli, Paolo
    Moeini, Seyed Sepehr
    Gasperi, Tecla
    Bernini, Roberta
    Incerpi, Sandra
    Tofani, Daniela
    MOLECULES, 2020, 25 (14):
  • [38] Synthesis and immunosuppressive activity of new artemisinin derivatives.: Part 2:: 2-[12(β or α)-dihydroartemisinoxymethyl-(or 1′-ethyl)]phenoxyl propionic acids and esters
    Yang, Zhong-Shun
    Wang, Jun-Xia
    Zhou, Yu
    Zuo, Han-Ping
    Li, Ying
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (23) : 8043 - 8049
  • [39] Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids derivatives
    Alice Maria Rolim Bernardino
    Alexandre Reis de Azevedo
    Luiz Carlos da Silva Pinheiro
    Júlio Cesar Borges
    Vinícius Lucio Carvalho
    Milene Dias Miranda
    Marcelo Damião Ferreira de Meneses
    Marcelo Nascimento
    Davis Ferreira
    Moacyr Alcoforado Rebello
    Viveca Antonia Giongo Galvão da Silva
    Izabel Christina Palmer Paixão de Frugulhetti
    Medicinal Chemistry Research, 2007, 16 : 352 - 369
  • [40] Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acids derivatives
    Rolim Bernardino, Alice Maria
    Reis de Azevedo, Alexandre
    da Silva Pinheiro, Luiz Carlos
    Cesar Borges, Julio
    Lucio Carvalho, Vinicius
    Dias Miranda, Milene
    Ferreira de Meneses, Marcelo Damiao
    Nascimento, Marcelo
    Ferreira, Davis
    Alcoforado Rebello, Moacyr
    Giongo Galvao da Silva, Viveca Antonia
    de Frugulhetti, Izabel Christina Palmer Paixao
    MEDICINAL CHEMISTRY RESEARCH, 2007, 16 (7-9) : 352 - 369