Preparation of Benzoyloxy Benzophenone Derivatives and Their Inhibitory Effects of ICAM-1 Expression

被引：17

作者：

Kwon, Eun Mi ^{[1
,2
]}

Kim, Cheol Gi ^{[1
,2
]}

Goh, Ah Ra ^{[3
,4
]}

Park, Jinseu ^{[3
,4
]}

Jun, Jong-Gab ^{[1
,2
]}

机构：

[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea

[2] Hallym Univ, Inst Nat Med, Chunchon 200702, South Korea

[3] Hallym Univ, Dept Biomed Sci, Chunchon 200702, South Korea

[4] Hallym Univ, Res Inst Biosci & Biotechnol, Chunchon 200702, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2012年 / 33卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

Benzoyloxy benzophenone; ICAM-1; Lewis acid; Fries rearrangement; Regioselectivity; AROMATIC REARRANGEMENTS; FRIES REARRANGEMENT; ADHESION MOLECULES; INTERFERON-GAMMA; BENZENE SERIES; INFLAMMATION; ALPHA;

D O I：

10.5012/bkcs.2012.33.6.1939

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Benzoyloxy benzophenone derivatives were prepared in 3 steps including DCC coupling, Fries rearrangement and esterification from benzoic acids in 24-89% total yields. Among the prepared 12 benzophenone analogues 1a-1l, the compound 1b having three chloro groups at the para position showed maximum inhibitory effects of ICAM-1 expression but, 1a which have no substituents at all showed no inhibitory activity. This study provides the evidences that benzoyloxy benzophenone derivative, 1b may exert its anti-inflammatory activity by suppressing IFN-gamma-induced ICAM-1 expression.

引用

页码：1939 / 1944

页数：6

共 15 条

[1] MARKED SYNERGISM BETWEEN TUMOR NECROSIS FACTOR-ALPHA AND INTERFERON-GAMMA IN REGULATION OF KERATINOCYTE-DERIVED ADHESION MOLECULES AND CHEMOTACTIC FACTORS [J].

BARKER, JNWN ;

SARMA, V ;

MITRA, RS ;

DIXIT, VM ;

NICKOLOFF, BJ .

JOURNAL OF CLINICAL INVESTIGATION, 1990, 85 (02) :605-608

[2] Molecular mechanisms of leukocyte trafficking in T-cell-mediated skin inflammation: insights from intravital imaging [J].

Deane, James A. ;

Hickey, Michael J. .

EXPERT REVIEWS IN MOLECULAR MEDICINE, 2009, 11

[3] AROMATIC REARRANGEMENTS IN BENZENE SERIES .2. FRIES REARRANGEMENT OF 4-BIPHENYLYL BIPHENYL-4-CARBOXYLATE [J].

DEWAR, MJS ;

HART, LS .

TETRAHEDRON, 1970, 26 (04) :1001-&

[4] AROMATIC REARRANGEMENTS IN BENZENE SERIES .1. FRIES REARRANGEMENT OF PHENYL BENZOATE - BENZOYLATION OF PHENOL [J].

DEWAR, MJS ;

HART, LS .

TETRAHEDRON, 1970, 26 (04) :973-&

[5] ADHESION OF T-LYMPHOBLASTS TO EPIDERMAL-KERATINOCYTES IS REGULATED BY INTERFERON-GAMMA AND IS MEDIATED BY INTERCELLULAR-ADHESION MOLECULE-1 (ICAM-1) [J].

DUSTIN, ML ;

SINGER, KH ;

TUCK, DT ;

SPRINGER, TA .

JOURNAL OF EXPERIMENTAL MEDICINE, 1988, 167 (04) :1323-1340

[6]

Jiri J., 1991, Csech CS, V271, P185, Patent No. 1991271185

[7] TUMOR NECROSIS FACTOR-BETA AND ULTRAVIOLET-RADIATION ARE POTENT REGULATORS OF HUMAN KERATINOCYTE ICAM-1 EXPRESSION [J].

KRUTMANN, J ;

KOCK, A ;

SCHAUER, E ;

PARLOW, F ;

MOLLER, A ;

KAPP, A ;

FORSTER, E ;

SCHOPF, E ;

LUGER, TA .

JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1990, 95 (02) :127-131

[8] Casuarinin suppresses TNF-α-induced ICAM-1 expression via blockade of NF-κB activation in HaCaT cells [J].

Kwon, Dong-Joo ;

Bae, Young-Soo ;

Ju, Sung Mi ;

Goh, Ah Ra ;

Choi, Soo Young ;

Park, Jinseu .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2011, 409 (04) :780-785

[9]

LAWLEY TJ, 1991, SEMIN DERMATOL, V10, P256

[10] Modeling cyclooxygenase inhibition.: Implication of active site hydration on the selectivity of ketoprofen analogues [J].

Palomer, A ;

Pérez, JJ ;

Navea, S ;

Llorens, O ;

Pascual, J ;

García, L ;

Mauleón, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (11) :2280-2284

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