Design and synthesis of 3,5-disubstituted 1,2,4-oxadiazole containing retinoids from a retinoic acid receptor agonist

被引：7

作者：

Das, Bhaskar C. ^{[1
,2
]}

Tang, Xiang-Ying ^{[2
]}

Sanyal, Swarnava ^{[2
]}

Mohapatra, Seetaram ^{[2
]}

Rogler, Patrick ^{[2
]}

Nayak, Sabita ^{[2
,4
]}

Evans, Todd ^{[3
]}

机构：

[1] Albert Einstein Coll Med, Dept Nucl Med, Bronx, NY 10461 USA

[2] Albert Einstein Coll Med, Dept Dev & Mol Biol, Bronx, NY 10461 USA

[3] Cornell Univ, Dept Surg, Weill Cornell Med Coll, New York, NY 10065 USA

[4] Ravenshaw Univ, Cuttack 753003, Orissa, India

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 19期

关键词：

DERIVATIVES; ESTERS; 4-HPR;

D O I：

10.1016/j.tetlet.2011.03.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We previously synthesized novel retinoid libraries, and after screening for bioactivity found one compound BT10 that functions as a specific agonist for retinoic acid receptors. This lead compound was further derivatized using SAR and LRD to obtain 3,5-disubstituted-1,2,4-oxadiazole-containing retinoids. The new oxadiazole (amide bioisosters)-containing retinoids (compounds 1, 2, 3, 4, 5, and 6) were synthesized in 42-65% yield by reacting with (E)-4-((3-ethy1,2-4,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid and phenyl substituted amidoxime in DMF using CDI as the coupling reagent. The biological activities of the synthesized compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2433 / 2435

页数：3

共 24 条

[1] RAR and RXR modulation in cancer and metabolic disease [J].

Altucci, Lucia ;

Leibowitz, Mark D. ;

Ogilvie, Kathleen M. ;

de Lera, Angel R. ;

Gronemeyer, Hinrich .

NATURE REVIEWS DRUG DISCOVERY, 2007, 6 (10) :793-810

[2]

Das B. C., MOL BIOSYSTEM UNPUB

[3] Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid [J].

Das, Bhaskar C. ;

Kabalka, George W. .

TETRAHEDRON LETTERS, 2008, 49 (32) :4695-4696

[4] Design, synthesis of novel peptidomimetic derivatives of 4-HPR for rhabdoid tumors [J].

Das, Bhaskar C. ;

Smith, Melissa E. ;

Kalpana, Ganjam V. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (14) :4177-4180

[5] Design and synthesis of 4-HPR derivatives for rhabdoid tumors [J].

Das, Bhaskar C. ;

Smith, Melissa E. ;

Kalpana, Ganjam V. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (13) :3805-3808

[6] A Forward Chemical Screen in Zebrafish Identifies a Retinoic Acid Derivative with Receptor Specificity [J].

Das, Bhaskar C. ;

McCartin, Kellie ;

Liu, Ting-Chun ;

Peterson, Randall T. ;

Evans, Todd .

PLOS ONE, 2010, 5 (03)

[7] Design and synthesis of α-aminonitrile-functionalized novel retinoids [J].

Das, Bhaskar C. ;

Anguiano, Jaime ;

Mahalingam, Sakkarapalayam M. .

TETRAHEDRON LETTERS, 2009, 50 (40) :5670-5672

[8] Design and synthesis of (E)-1-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl-4-substituted benzenes from 1-(2,6,6-trimethylcyclohex-1-enyl)ethanol [J].

Das, Bhaskar C. ;

Mahalingam, Sakkarapalayam M. ;

Evans, Todd ;

Kabalka, George W. ;

Anguiano, J. ;

Hema, K. .

CHEMICAL COMMUNICATIONS, 2009, (16) :2133-2135

[9] CONFORMATIONALLY RESTRICTED RETINOIDS [J].

DAWSON, MI ;

HOBBS, PD ;

DERDZINSKI, K ;

CHAN, RLS ;

GRUBER, J ;

CHAO, WR ;

SMITH, S ;

THIES, RW ;

SCHIFF, LJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (11) :1516-1531

[10]

Groziak MP, 2000, PROG HET CH, V12, P1, DOI 10.1016/S0959-6380(00)80003-3

← 1 2 3 →