GLYCOLAMIDE ESTERS OF 6-METHOXY-2-NAPHTHYLACETIC ACID AS POTENTIAL PRO-DRUGS - SYNTHETIC AND SPECTRAL STUDIES

被引:0
|
作者
WADHWA, LK [1 ]
SHARMA, PD [1 ]
机构
[1] PANJAB UNIV,DEPT PHARMACEUT SCI,CHANDIGARH 160014,INDIA
来源
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 1995年 / 34卷 / 05期
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
6-Methoxy-2-naphthylacetic acid (6-MNA; 1), the active metabolite of newly developed NSAID nabumetone (2) has been modified using prodrug approach. A number of glycolamide ester prodrugs of 6-MNA have been synthesized by masking the free carboxyl group of 6-MNA, mainly responsible for gastric damage, in order to obtain NSAIDs with improved therapeutic index. The structures of these derivatives have been established on the basis of elemental and spectral analyses.
引用
收藏
页码:408 / 415
页数:8
相关论文
共 37 条
  • [21] EFFECTS OF NABUMETONE AND ITS ACTIVE METABOLITE, 6-METHOXY-2-NAPHTHYLACETIC ACID (6-MNA), ON THROMBOXANE BIOSYNTHESIS IN-VIVO AND IN-VITRO
    PATRIGNANI, P
    CIPOLLONE, F
    DISIPIO, M
    DIFEBBO, C
    PORRECA, E
    GANCI, A
    DELBIANCO, A
    CUCCURULLO, F
    PATRONO, C
    BRITISH JOURNAL OF PHARMACOLOGY, 1994, 111 : P76 - P76
  • [22] A Predominate Role of CYP1A2 for the Metabolism of Nabumetone to the Active Metabolite, 6-Methoxy-2-naphthylacetic Acid, in Human Liver Microsomes
    Turpeinen, Miia
    Hofmann, Ute
    Klein, Kathrin
    Muerdter, Thomas
    Schwab, Matthias
    Zanger, Ulrich M.
    DRUG METABOLISM AND DISPOSITION, 2009, 37 (05) : 1017 - 1024
  • [23] Effect of 6-methoxy-2-naphthylacetic acid (6MNA), the active metabolite of nabumetone, on the glycosaminoglycan synthesis of canine articular cartilage in vitro - Comparison with other nonsteroidal anti-inflammatory drugs
    Gentry, C
    Blower, P
    Spangler, R
    CLINICAL DRUG INVESTIGATION, 1995, 10 (06) : 355 - 364
  • [24] Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone
    Canudas, N
    Zamora, D
    Villamizar, JE
    Fuentes, J
    Castelli, C
    Taddei, A
    PHARMAZIE, 2005, 60 (08): : 604 - 608
  • [25] A metabolic pathway for the prodrug nabumetone to the pharmacologically active metabolite, 6-methoxy-2-naphthylacetic acid (6-MNA) by non-cytochrome P450 enzymes
    Matsumoto, Kaori
    Hasegawa, Tetsuya
    Ohara, Kosuke
    Takei, Chihiro
    Kamei, Tomoyo
    Koyanagi, Junichi
    Takahashi, Tamiko
    Akimoto, Masayuki
    XENOBIOTICA, 2020, 50 (07) : 783 - 792
  • [26] Simplex optimization of the variables affecting the micelle-stabilized room temperature phosphorescence of 6-methoxy-2-naphthylacetic acid and its kinetic determination in human urine
    Pulgarin, JAM
    Molina, AA
    Pardo, MTA
    ANALYTICAL BIOCHEMISTRY, 2005, 339 (01) : 157 - 164
  • [27] Simultaneous analysis of naproxen, nabumetone and its major metabolite 6-methoxy-2-naphthylacetic acid in pharmaceuticals and human urine by high-performance liquid chromatography
    Mikami, E
    Goto, T
    Ohno, T
    Matsumoto, H
    Nishida, M
    JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2000, 23 (05) : 917 - 925
  • [28] ENOL ESTERS AS POTENTIAL PRO-DRUGS .2. INVITRO AQUEOUS STABILITY AND ENZYME-MEDIATED HYDROLYSIS OF SEVERAL ENOL ESTERS OF ACETOPHENONE
    PATEL, JP
    REPTA, AJ
    INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1981, 9 (01) : 29 - 47
  • [29] High-throughput LC-MS/MS assay for 6-methoxy-2-naphthylacetic acid, an active metabolite of nabumetone in human plasma and its application to bioequivalence study
    Patel, Bhavin N.
    Sharma, Naveen
    Sanyal, Mallika
    Prasad, Arpana
    Shrivastav, Pranav S.
    BIOMEDICAL CHROMATOGRAPHY, 2008, 22 (11) : 1213 - 1224
  • [30] CONCENTRATION OF 6-METHOXY-2-NAPHTHYLACETIC ACID IN PLASMA, SYNOVIAL-FLUID AND SURROUNDING TISSUES OF PATIENTS WITH RHEUMATOID-ARTHRITIS OR OSTEOARTHRITIS AFTER A 4-DAYS-TREATMENT WITH NABUMETONE (ARTHAXAN)
    MIEHLKE, RK
    SCHNEIDER, S
    SORGEL, F
    MUTH, P
    HENSCHKE, F
    FEDDER, M
    ZEITSCHRIFT FUR RHEUMATOLOGIE, 1991, 50 (02): : 103 - 108