Synthesis, structure elucidation, and anti-inflammatory/anti-cancer/anti-bacterial activities of novel (Z)-3-adamantyl-1-aryl-prop/but-2-en-1-ones

被引：12

作者：

Kalita, Utpalparna ^{[1
]}

Kaping, Shunan ^{[1
]}

Nongkynrih, Revinus ^{[2
]}

Sunn, Melboureen ^{[2
]}

Boiss, Ivee ^{[2
]}

Singha, Laishram Indira

Vishwakarma, Jai Narain ^{[1
,2
]}

机构：

[1] Assam Don Bosco Univ, Dept Chem Sci, Organ Res Lab, Gauhati 781017, Assam, India

[2] St Anthonys Coll, Dept Biotechnol, Shillong 793001, Meghalaya, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2015年 / 24卷 / 01期

关键词：

Enaminone; Adamantane; Anti-inflammatory activity; Anti-cancer; Anti-bacterial; ADDITION-ELIMINATION REACTIONS; NITRIC-OXIDE SYNTHASE; ANTIINFLAMMATORY ACTIVITIES; ANTIMICROBIAL ACTIVITY; ALPHA PRODUCTION; ENAMINONES; ADAMANTANE; DERIVATIVES; ANTITUMOR; ROUTE;

D O I：

10.1007/s00044-014-1086-x

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of hitherto unreported (Z)-3-adamantyl-1-aryl-prop/but-2-en-1-ones (4a-j) were prepared from formylated/acetylated active proton compounds (2a-j) and 1-adamantanamine (3) under microwave irradiation in good to excellent yields. The structures of 4a-j have been unequivocally established with the help of spectral and analytical data. All the products were found to exist in Z form which was also supported by X-ray crystallographic studies. Compounds 4a-j were assessed for their biological activities by testing their anti-inflammatory, anti-cancer, and anti-bacterial properties. The compounds 4h and 4i showed highest anti-inflammatory properties, while the compounds 4a and 4g were found to be the most cytotoxic and may have anti-cancer properties. However, none of the compounds exhibited anti-bacterial activity.

引用

页码：32 / 50

页数：19

共 66 条

[51]

Riyadh SM, 2008, HETEROCYCLES, V75, P1849

[52] Enaminones as Building Blocks for the Synthesis of Substituted Pyrazoles with Antitumor and Antimicrobial Activities [J].

Riyadh, Sayed M. .

MOLECULES, 2011, 16 (02) :1834-1853

[53] NITRIC-OXIDE ACTIVATES CYCLOOXYGENASE ENZYMES [J].

SALVEMINI, D ;

MISKO, TP ;

MASFERRER, JL ;

SEIBERT, K ;

CURRIE, MG ;

NEEDLEMAN, P .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :7240-7244

[54] EVALUATION OF STRAIN IN HYDROCARBONS - STRAIN IN ADAMANTANE AND ITS ORIGIN [J].

SCHLEYER, PV ;

WILLIAMS, JE ;

BLANCHARD, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2377-+

[55] Copper-Catalyzed Selective Synthesis of Highly Substituted Pyridones by the Reaction of Enaminones with Alkynes [J].

Shao, Yushang ;

Yao, Wenjuan ;

Liu, Jun ;

Zhu, Kai ;

Li, Yanzhong .

SYNTHESIS-STUTTGART, 2012, 44 (21) :3301-3306

[56]

SHIBATA Y, 1995, CHEM PHARM BULL, V43, P177

[57] 1-ADAMANTANECARBOXYLIC ACID AMIDE OF 4-AMINOANTIPYRINE [J].

SPANO, R ;

LINARI, G ;

MARRI, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (03) :554-&

[58] Utilisation of chiral enaminones and azomethine imines in the synthesis of functionalised pyrazoles [J].

Svete, Jurij .

ARKIVOC, 2006, :35-56

[59] Synthesis of New Compounds Combining Adamantanamine and Monoterpene Fragments and their Antiviral Activity Against Influenza Virus A(H1N1)pdm09 [J].

Teplov, George V. ;

Suslov, Evgeny V. ;

Zarubaev, Vladimir V. ;

Shtro, Anna A. ;

Karpinskaya, Liubov A. ;

Rogachev, Artem D. ;

Korchagina, Dina V. ;

Volcho, Konstantin P. ;

Salakhutdinov, Nariman F. ;

Kiselev, Oleg I. .

LETTERS IN DRUG DESIGN & DISCOVERY, 2013, 10 (06) :477-485

[60] Synthesis and anti-bacterial activities of novel 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines and bis-(5-isonicotinoyl-1,2,3,4-tetrahydropyrimidines) [J].

Vishwakarma, J. N. ;

Dutta, M. C. ;

Chanda, K. ;

Das, Bhaskar ;

Laskar, M. A. ;

Nongkhlaw, R. L. .

ARKIVOC, 2009, :131-141

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