Synthesis of Heterocyclic Analogs of α-aminoadipic Acid and its Esters Based on Imidazo[2,1-b][1,3]Thiazole

被引：2

作者：

Sackus, Algirdas ^{[1
,2
]}

Brickute, Diana ^{[1
]}

Paliulis, Osvaldas ^{[2
]}

Slok, Frank Abildgaard ^{[3
]}

机构：

[1] Kaunas Univ Technol, Dept Organ Chem, LT-50254 Kaunas, Lithuania

[2] Kaunas Univ Technol, Inst Synthet Chem, LT-50254 Kaunas, Lithuania

[3] Vipergen ApS, DK-1610 Copenhagen, Denmark

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2015年 / 52卷 / 04期

关键词：

BIS-LACTIM ETHERS; AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; BIOLOGICAL-ACTIVITY; DERIVATIVES; CONSTRUCTION; BROMINATION; SYSTEM;

D O I：

10.1002/jhet.2090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the preparation of heterocyclic analogs of alpha-aminoadipic acid and its esters based on the imidazo [2,1-b][1,3]thiazole ring system was developed. In this method, free-radical bromination of ethyl 6-methylimidazo [2,1-b][1,3]thiazole-5-carboxylate with NBS afforded a versatile building block, ethyl 6-bromomethylimidazo[2,1-b][1,3] thiazole-5-carboxylate. Coupling of ethyl 6-bromomethylimidazo[2,1-b][1,3] thiazole-5-carboxylate with Schollkopf's chiral auxiliary followed by acidic hydrolysis generated ethyl 6-[(2S)-2-amino-3-methoxy-3-oxopropyl] imidazo[2,1-b][1,3]thiazole-5-carboxylate. A similar procedure using diethyl (Boc-amino) malonate yielded racemic 2-amino-3-[(5-ethoxycarbonyl)imidazo[2,1-b][1,3]thiazol-6-yl] propanoic acid.

引用

页码：1032 / 1036

页数：5

共 38 条

[1]

Aissaoui H., 2009, [No title captured], Patent No. [WO/2009/016560 A2, 2009016560, WO 2009016560A2]

[2]

Al Hariri M, 1998, EUR J ORG CHEM, V1998, P593

[3] 6-thienyl and 6-phenylimidazo[2,1-b]thiazoles as inhibitors of mitochondrial NADH dehydrogenase [J].

Andreani, A ;

Rambaldi, M ;

Leoni, A ;

Morigi, R ;

Locatelli, A ;

Giorgi, G ;

Lenaz, G ;

Ghelli, A ;

Degli Esposti, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (10) :883-889

[4] Synthesis and antitumor activity of guanylhydrazones from 6-(2,4-dichloro-5-nitrophenyl)imidazo[2,1-b]thiazoles and 6-pyridylimidazo[2,1-b]thiazoles [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Farruggia, Giovanna ;

Stefanelli, Claudio ;

Masotti, Lanfranco ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (26) :7897-7901

[5]

Bothner-By A.A., 1965, Advances in Magnetic and Optical Resonance, P195, DOI 10.1016/b978-1-4832-3114-3.50011-8

[6] Imidazo[2,1-b]thiazole system:: A scaffold endowing dihydropyridines with selective cardiodepressant activity [J].

Budriesi, Roberta ;

Ioan, Pierfranco ;

Locatelli, Alessandra ;

Cosconati, Sandro ;

Leoni, Alberto ;

Ugenti, Maria P. ;

Andreani, Aldo ;

Di Toro, Rosanna ;

Bedini, Andrea ;

Spampinato, Santi ;

Marinelli, Luciana ;

Novellino, Ettore ;

Chiarini, Alberto .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) :1592-1600

[7]

Calí P, 2002, SYNTHESIS-STUTTGART, P63

[8] Catalytic, asymmetric, "interrupted" Feist-Benary reactions [J].

Calter, MA ;

Phillips, RM ;

Flaschenriem, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) :14566-14567

[9] SYNTHESIS AND ANTIMYCOBACTERIAL ACTIVITY OF NEW IMIDAZO[2,1-B]THIAZOLE DERIVATIVES [J].

CESUR, Z ;

GUNER, H ;

OTUK, G .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (12) :981-983

[10]

Ding H., 2012, MOLECULES, V17, P4073

← 1 2 3 4 →