Straightforward synthesis of novel spiroether derivatives

被引:13
作者
Bobrovskaya, Olga V. [1 ]
Russkih, Aleksandr A. [1 ]
Yankin, Andrei N. [2 ]
Dmitriev, Maksim V. [3 ]
Bunev, Aleksandr S. [4 ]
Gein, Vladimir L. [1 ]
机构
[1] Perm State Pharmaceut Acad, Perm, Russia
[2] ITMO Univ, Dept Phys & Engn, St Petersburg, Russia
[3] Perm State Natl Res Univ, Dept Chem, Perm, Russia
[4] Togliatti State Univ, Medicinal Chem Ctr, Tolyatti, Russia
关键词
Alloxan; cytotoxity; heterocycles; pyrimidine; spiroethers;
D O I
10.1080/00397911.2021.1903930
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the first full synthesis of novel spiroether derivatives via reaction of 4-oxobut-2-enoates and alloxan. Our synthesis features the single-step assembly, mild reaction conditions, good yields, high diastereoselectivity, operational simplicity, and the absence of tedious separation procedures. Most of the prepared compounds possessed moderate growth inhibitory effects on human alveolar adenocarcinoma (A549), malignant melanoma (A375), ovarian adenocarcinoma (SK-OV-3), and fibrosarcoma (HT-1080) cell lines.
引用
收藏
页码:1731 / 1741
页数:11
相关论文
共 29 条
[1]  
[Anonymous], 2008, ACTA CRYSTALLOGR A
[2]   ISOLATION AND STRUCTURE OF PSEUROTIN-A, A MICROBIAL METABOLITE OF PSEUDEUROTIUM-OVALIS STOLK WITH AN UNUSUAL HETEROSPIROCYCLIC SYSTEM [J].
BLOCH, P ;
TAMM, C .
HELVETICA CHIMICA ACTA, 1981, 64 (01) :304-315
[3]   NATURALLY-OCCURRING TERPENE DERIVATIVES .390. HIRSUTINOLIDES AND OTHER SESQUITERPENE LACTONES FROM VERNONIA SPECIES [J].
BOHLMANN, F ;
ZDERO, C ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1982, 21 (03) :695-699
[4]   OLEX2: a complete structure solution, refinement and analysis program [J].
Dolomanov, Oleg V. ;
Bourhis, Luc J. ;
Gildea, Richard J. ;
Howard, Judith A. K. ;
Puschmann, Horst .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341
[5]   Cascade Assembling of Isatins and Barbituric Acids: Facile and Efficient Way to 2H-Dispiro[indole-3,5-furo[2,3-d]pyrimidine-6,5-pyrimidine]-2,2,2,4,4,6-(1H,1H,1H,3H,3H)-hexone Scaffold [J].
Elinson, Michail N. ;
Merkulova, Valentina M. ;
Ilovaisky, Alexey I. ;
Nikishin, Gennady I. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) :1236-1241
[6]  
GEIN VL, 2017, RUSS J ORG CHEM, V53
[7]   One-pot multicomponent synthesis of highly substituted bicyclo[2.2.2]octane derivatives using bismuth nitrate as a catalyst [J].
Gein, Vladimir L. ;
Yankin, Andrei N. ;
Nosova, Natalia V. ;
Dmitriev, Maxim V. ;
Slepukhin, Pavel A. .
TETRAHEDRON LETTERS, 2016, 57 (22) :2441-2444
[8]   Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls [J].
Giarrusso, James ;
Do, Dung T. ;
Johnson, Jeffrey S. .
ORGANIC LETTERS, 2017, 19 (12) :3107-3110
[9]  
HIRASAWA Y, 2011, ORG LETT, V12
[10]   A Convergent Approach to Diverse Spiroethers through Stereoselective Trapping of Rhodium Carbenoids with Gold-Activated Alkynols [J].
Hunter, Arianne C. ;
Schlitzer, Steven C. ;
Stevens, Joseph C. ;
Almutwalli, Bilal ;
Sharma, Indrajeet .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) :2744-2752