gewald reaction
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Molecules ◽  
2022 ◽  
Vol 27 (1) ◽  
pp. 321
Author(s):  
Farhana Islam ◽  
Arpit Doshi ◽  
Andrew J. Robles ◽  
Tasdique M. Quadery ◽  
Xin Zhang ◽  
...  

A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines were designed and synthesized and their biological activities were evaluated. Synthesis involved the Gewald reaction to synthesize ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate ring, and SNAr reactions. Compound 4 was 1.6- and ~7-fold more potent than the lead compound 1 in cell proliferation and microtubule depolymerization assays, respectively. Compounds 4, 5 and 7 showed the most potent antiproliferative effects (IC50 values < 40 nM), while compounds 6, 8, 10, 12 and 13 had lower antiproliferative potencies (IC50 values of 53–125 nM). Additionally, compounds 4–8, 10 and 12–13 circumvented Pgp and βIII-tubulin mediated drug resistance, mechanisms that diminish the clinical efficacy of paclitaxel (PTX). In the NCI-60 cell line panel, compound 4 exhibited an average GI50 of ~10 nM in the 40 most sensitive cell lines. Compound 4 demonstrated statistically significant antitumor effects in a murine MDA-MB-435 xenograft model.



2021 ◽  
Vol 62 (1) ◽  
pp. 183
Author(s):  
O. Shyyka ◽  
M. Svyrydenko ◽  
M. Tupychak ◽  
N. Pokhodylo ◽  
M. Obushak
Keyword(s):  




Synlett ◽  
2020 ◽  
Author(s):  
Kevin Hung ◽  
Fumiaki Yokokawa ◽  
Yugang Liu ◽  
Oliver Simon ◽  
Lei Zhang ◽  
...  

A synthesis of the first-in-class pan-serotype dengue virus inhibitor NITD-688 is presented. The Gewald reaction of N-(tert-butoxycarbonyl)-6,6-dimethylpiperidin-3-one with malononitrile and sulfur in the presence of l-proline as a catalyst gave tert-butyl 2-amino-3-cyano-6,6-dimethyl-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate. This was coupled with [4-(aminosulfonyl)phenyl]acetic acid by using propane­phosphonic acid anhydride. A subsequent reductive alkylation with cyclohexanecarboxaldehyde gave NITD-688. Preliminary results of our attempts to control the regioselectivity of the Gewald synthesis of the 2-amino-3-cyanothiophene core are also presented.





2020 ◽  
Vol 41 (3) ◽  
pp. 301-309
Author(s):  
Saeed Bagherpour ◽  
Mohammad M. Mojtahedi ◽  
M. Saeed Abaee
Keyword(s):  


2019 ◽  
Vol 56 (10) ◽  
pp. 2787-2795 ◽  
Author(s):  
Mohamed A. El‐Borai ◽  
Hala F. Rizk ◽  
Seham A. Ibrahim ◽  
Amira K. Fares


2018 ◽  
Vol 40 (2) ◽  
pp. 195-208 ◽  
Author(s):  
Kotthireddy Kavitha ◽  
Devulapally Srikrishna ◽  
Pramod Kumar Dubey ◽  
Pasula Aparna




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