Keywords
1 3-dielectrophiles
aza-Michael addition
bis(aldehyde)
heterocyclization
in vitro antibacterial screening
multicomponent reactions
pyrazolo[1,5-a]pyrimidine
α-unsaturated nitriles
Abstract
A three-component protocol was adopted to efficiently prepare new bis(pyrazolo[1,5-a]pyrimidines) linked to different spacers in 80-92% yields from 1H-pyrazole-3,5-diamines, malononitrile and bis(aldehydes). The p-xylene-linked bis(pyrimidine) bearing 3-positioned 4-methoxy-benzyl substituent had the best antibacterial activity with MIC / MBC values up to 2.2 / 4.4 µm.
References
1.
Martelli G., Giacomini D.
European Journal of Medicinal Chemistry,
2018
2.
Selleri S., Bruni F., Costagli C., Costanzo A., Guerrini G., Ciciani G., Gratteri P., Bonaccini C., Malmberg Aiello P., Besnard F., Renard S., Costa B., Martini C.
Journal of Medicinal Chemistry,
2002
3.
Selleri S., Bruni F., Costagli C., Costanzo A., Guerrini G., Ciciani G., Gratteri P., Besnard F., Costa B., Montali M., Martini C., Fohlin J., De Siena G., Aiello P.M.
Journal of Medicinal Chemistry,
2005
4.
Heathcote D.A., Patel H., Kroll S.H., Hazel P., Periyasamy M., Alikian M., Kanneganti S.K., Jogalekar A.S., Scheiper B., Barbazanges M., Blum A., Brackow J., Siwicka A., Pace R.D., Fuchter M.J., et. al.
Journal of Medicinal Chemistry,
2010
5.
Abdelhamid A.O., El-Idreesy T.T., Abdelriheem N.A., Dawoud H.R.
Journal of Heterocyclic Chemistry,
2015
6.
Sanad S.M., Mekky A.E.
Chemistry and Biodiversity,
2021
7.
Bloom D.E., Cadarette D.
Frontiers in Immunology,
2019
8.
Mekky A.E., Sanad S.M.
Polycyclic Aromatic Compounds,
2019
9.
Mekky A.E., Ahmed M.S., Sanad S.M., Abdallah Z.A.
Synthetic Communications,
2021
10.
Metwally N.H., Koraa T.H., Sanad S.M.
Synthetic Communications,
2022
11.
Kamal A., Rahim A., Riyaz S., Poornachandra Y., Balakrishna M., Kumar C.G., Hussaini S.M., Sridhar B., Machiraju P.K.
Organic and Biomolecular Chemistry,
2015
12.
Hassan A.S., Morsy N.M., Awad H.M., Ragab A.
Journal of the Iranian Chemical Society,
2021
13.
Ayman R., Radwan A.M., Elmetwally A.M., Ammar Y.A., Ragab A.
Archiv der Pharmazie,
2022
14.
Vaquero J.J., Fuentes L., Del Castillo J.C., Pérez M.I., García J.L., Soto J.L.
Synthesis,
1987
15.
Mohammad H., Reddy P.V., Monteleone D., Mayhoub A.S., Cushman M., Seleem M.N.
European Journal of Medicinal Chemistry,
2015
16.
Zhang J., Peng J., Wang T., Wang P., Zhang Z.
Journal of Molecular Structure,
2016
17.
Cherukupalli S., Karpoormath R., Chandrasekaran B., Hampannavar G.A., Thapliyal N., Palakollu V.N.
European Journal of Medicinal Chemistry,
2017
18.
Hassan A.S., Mady M.F., Awad H.M., Hafez T.S.
Chinese Chemical Letters,
2017
19.
Wang X., Magnuson S., Pastor R., Fan E., Hu H., Tsui V., Deng W., Murray J., Steffek M., Wallweber H., Moffat J., Drummond J., Chan G., Harstad E., Ebens A.J., et. al.
Bioorganic and Medicinal Chemistry Letters,
2013
20.
Gommermann N., Buehlmayer P., von Matt A., Breitenstein W., Masuya K., Pirard B., Furet P., Cowan-Jacob S.W., Weckbecker G.
Bioorganic and Medicinal Chemistry Letters,
2010
21.
Fahim A.M., Farag A.M.
Journal of Molecular Structure,
2020
22.
Powell D., Gopalsamy A., Wang Y.D., Zhang N., Miranda M., McGinnis J.P., Rabindran S.K.
Bioorganic and Medicinal Chemistry Letters,
2007
23.
Sanad S.M., Mekky A.E.
Mendeleev Communications,
2021
24.
Sadek K.U., Mekheimer R.A., Mohamed T.M., Moustafa M.S., Elnagdi M.H.
Beilstein Journal of Organic Chemistry,
2012
25.
Fraley M.E., Rubino R.S., Hoffman W.F., Hambaugh S.R., Arrington K.L., Hungate R.W., Bilodeau M.T., Tebben A.J., Rutledge R.Z., Kendall R.L., McFall R.C., Huckle W.R., Coll K.E., Thomas K.A.
Bioorganic and Medicinal Chemistry Letters,
2002
26.
Mekky A.E., Sanad S.M., Abdelfattah A.M.
Mendeleev Communications,
2022
27.
Baig M.Z., Oh H., Son Y.
Dyes and Pigments,
2022
28.
Al-Jumaili M.H., Hamad A.A., Hashem H.E., Hussein A.D., Muhaidi M.J., Ahmed M.A., ALBANAA A.H., Siddique F., Bakr E.A.
Journal of Molecular Structure,
2023