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. 2022 Oct;11(10):e202200169.
doi: 10.1002/open.202200169.

Antiproliferative Activity of (-)-Isopulegol-based 1,3-Oxazine, 1,3-Thiazine and 2,4-Diaminopyrimidine Derivatives

Fatima Z Bamou  1 , Tam M Le  1 , Bizhar A Tayeb  2 , Seyyed A S Tahaei  2 , Renáta Minorics  2 , István Zupkó  2 , Zsolt Szakonyi  1
Affiliations

Antiproliferative Activity of (-)-Isopulegol-based 1,3-Oxazine, 1,3-Thiazine and 2,4-Diaminopyrimidine Derivatives

Fatima Z Bamou et al. ChemistryOpen. 2022 Oct.

Abstract

A series of novel heterocyclic structures, namely 1,3-oxazines, 1,3-thiazines and 2,4-diaminopyrimidines, were designed and synthesised. The bioassay tests demonstrated that, among these analogues, 2,4-diaminopyridine derivatives showed significant antiproliferative activity against different human cancer cell lines (A2780, SiHa, HeLa, MCF-7 and MDA-MB-231). Pyrimidines substituted with N2 -(p-trifluoromethyl)aniline, in particular, displayed a potent inhibitory effect on the growth of cancer cells. Structure-activity relationships were also studied from the aspects of stereochemistry on the aminodiol moiety as well as exploring the effects of substituents on the pyrimidine scaffold.

Keywords: (+)-neoisopulegol; (−)-isopulegol; 1,3-oxazines; 1,3-thiazines; 2,4-diaminopyrimidines.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Preparation of (−)‐isopulegol‐based aminodiols 2 a, b and aminotriol 4.
Scheme 2
Scheme 2
Preparation of (−)‐isopulegol‐based aminodiol 6 and aminoalcohols 8 a, b.
Scheme 3
Scheme 3
Preparation of (+)‐neoisopulegol‐based aminodiols 10–12 and aminoalcohol 14.
Scheme 4
Scheme 4
Preparation of (16 a, b and oxazines 17 a–d.
Scheme 5
Scheme 5
Preparation of (−)‐isopulegol‐based pyrimidine derivatives 19–20.
Scheme 6
Scheme 6
Preparation of (−)‐isopulegol‐based pyrimidine derivatives 21–23.
Figure 1
Figure 1
Antiproliferative properties of the selected isopulegol‐based pyrimidine derivatives.
Figure 2
Figure 2
2D diagram of key binding interactions of hit (compound 20 b) with Aurora A.
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