Flow chemistry and polymer-supported pseudoenantiomeric acylating agents enable parallel kinetic resolution of chiral saturated N-heterocycles

ISSN:1755-4349ISSN:1755-433

Homohirāli aziridīni ar triazola aizvietotāju sānu ķēdē

Aprakstīti jauna tipa potenciāli bioloģiski aktīvi aziridīnu atvasinājum

Novel Chiral Aziridine-Triazole Conjugates

Synthesis of novel aziridine-triazole conjugates is discusse

Synthesis of Homochiral Aziridine-Triazole Conjugates

Aziridīna atvasinājumi ir zināmi kā pretvēža aģenti. Šajā darbā apskatīta jaunu aziridīna triazolilatvasinājumu sintēze, lietojot 1,3-dipolāro azīdu alkīnu ciklopievienošan

Aziridine - Triazole Conjugates as a Novel Class of MMP-2 Inhibitors

We report here the synthesis of a series of (aryltriazolyl)methylaziridines 1 and their evaluation as selective inhibitors of MMP-2.[2] They constitute a novel class of hydroxamic acid-free matrix metalloproteinase inhibitors

2-aizvietotu aziridīnu N-vinilēšana ar malonskābes atvasinājumiem

Šajā darbā pētītas N-aizvietotu aziridīnu sintēzes iespējas aziridīna karbonskābes metilestera un amīda reakcijās ar Meldrumskābes etoksimetilēnatvasinājumiem, (etoksimetilēn)malonnitrilu, etil(etoksimetilēn)cianoacetātu un (1-etoksietilidēn)malonnitrilu. Eksperimentāli noteikti optimālie reakcijas apstākļi, kas sevī ietver zemākos spirtus kā šķīdinātājus un temperatūras intervālu no 0 oC līdz +40 oC. Augstākās temperatūrās var novērot aziridīna cikla daļēju šķelšanos. Dotajos apstākļos aziridīna N-vinilēšanai piemērotas tikai cikliskās, no Meldrumskābes atvasinātās izejvielas. Acikliskie aktivētie alkoksimetilēnatvasinājumi pieprasa augstākas reakcijas temperatūras un tādejādi individuāli produkti no šīm reakcijām netika izdalīti. Piedāvāta lēta un vienkārša aziridīn-2-karboksamīda sintēzes metode no attiecīgā aziridīn-2-karbonitrila. Tā ideāli norit ūdens vidē, lietojot acetonu kā organokatalizator

Synthesis of Tetrahydronaphthyridines from Aldehydes and HARP Reagents via Radical Pictet–Spengler Reactions

The combination of aldehydes with newly designed HARP (halogen amine radical protocol) reagents gives access to α-substituted tetrahydronaphthyridines. By using different HARP reagents, various regioisomeric structures can be prepared in a single operation. These products, which are of high value in medicinal chemistry, are formed in a predictable manner via a formal Pictet–Spengler reaction of electron-poor pyridines that would not participate in the corresponding polar reactions

Triazolylmethyl Aziridines with Various Side Chain

More than hundred compounds from aziridine class shown certain biological activity. We report here the synthesis of racemic version of protected azidomethyl aziridine via easily accessible intermediates. Further, small combinatorial library of triazolylmethyl aziridines was obtained by CuAAC reaction and deprotection. To the best of our knowledge such aziridine derivatives have not been tested for their biological activities. Comparison of synthesis of racemic and enantiomerically pure series of products and their biological activities will be discussed

Discovery of Aziridine–Triazole Conjugates as Selective MMP-2 Inhibitors

A series of (aryltriazolyl)methylaziridines were synthesized and evaluated as selective inhibitors of matrix metalloproteinase-2. They constitute a novel class of hydroxamic acid-free matrix metalloproteinase inhibitors. The triazole fragment serves as a linker between the hydrophilic aziridine and the lipophilic part of the molecule. The best inhibition was observed with 1-(aziridin-2-ylmethyl)-4-(4-butylphenyl)-1H-1,2,3-triazole and 1-(aziridin-2-ylmethyl)-4-phenyl-1H-1,2,3-triazole that selectively inhibited MMP-2 at 73% in 20 μM concentration and at 75% in 10 μM concentration, respectively