Submission Details

Molecule(s):
O=c1cc(-c2cccc(Cl)c2)oc2cc(F)ccc12

LYN-UNI-b265e4fd-1

O=c1cc(-c2cccc(Cl)c2)oc2cc(F)ccc12

COc1ccc2c(=O)cc(-c3ccc(F)cc3)oc2c1

LYN-UNI-b265e4fd-2

COc1ccc2c(=O)cc(-c3ccc(F)cc3)oc2c1

O=c1cc(-c2cc(C(F)(F)F)cc(C(F)(F)F)c2)oc2cc(F)ccc12

LYN-UNI-b265e4fd-3

O=c1cc(-c2cc(C(F)(F)F)cc(C(F)(F)F)c2)oc2cc(F)ccc12

O=c1cc(C2CCCCC2)oc2cc(N3CCOCC3)ccc12

LYN-UNI-b265e4fd-4

O=c1cc(C2CCCCC2)oc2cc(N3CCOCC3)ccc12

O=c1cc(-c2ccc(F)cc2)oc2cc(F)ccc12

LYN-UNI-b265e4fd-5

O=c1cc(-c2ccc(F)cc2)oc2cc(F)ccc12

COc1ccc2c(=O)cc(-c3ccc(C(F)(F)F)cc3)oc2c1

LYN-UNI-b265e4fd-6

COc1ccc2c(=O)cc(-c3ccc(C(F)(F)F)cc3)oc2c1

COc1ccc2c(=O)cc(C3CCCCC3)oc2c1

LYN-UNI-b265e4fd-8

COc1ccc2c(=O)cc(C3CCCCC3)oc2c1

O=c1cc(-c2ccc(C(F)(F)F)cc2)oc2ccc(Br)cc12

LYN-UNI-b265e4fd-9

O=c1cc(-c2ccc(C(F)(F)F)cc2)oc2ccc(Br)cc12

O=c1cc(-c2ccc(C(F)(F)F)cc2)oc2cc(F)ccc12

LYN-UNI-b265e4fd-10

O=c1cc(-c2ccc(C(F)(F)F)cc2)oc2cc(F)ccc12


Design Rationale:

Chromones have been identified as privileged scaffolds in drug discovery and reported as antivirals in the treatment of HIV (1) Para substitution on the B ring has been reported as required to promote antiplasmodial activity and increase HIV-2 potency (2) Naturally occurring medicinal plant containing chromones have been shown to inhibit SARS-CoV-2 3CLpro activity and hence virus replication in computational screening (3) 1. Keri, R. S.; Budagumpi, S.; Pai, R. K.; Balakrishna, R. G., Chromones as a privileged scaffold in drug discovery: A review. European Journal of Medicinal Chemistry, 2014, 78, 340. 2. Casano, G.; Dumètre, A.; Pannecouque, C.; Hutter, S.; Azas, N.; Robin, M., Anti-HIV and antiplasmodial activity of original flavonoid derivatives. Bioorganic & Medicinal Chemistry, 2010, 18, 6012. 3. ul Qamar, M. T.; Alqahtani, S. M.; Alamri, M. A.; Chen, L.-L., Structural basis of SARS-CoV-2 3CLpro and anti-COVID-19 drug discovery from medicinal plants†. Journal of Pharmaceutical Analysis, 2020.

Other Notes:

I have some of these compounds readily accessible and the others can be simply remade. The synthesis of these compounds is simple and can be easily reproduced to produce a range of analogues (4, 5) 4. Abdel Ghani, S. B.; Mugisha, P. J.; Wilcox, J. C.; Gado, E. A. M.; Medu, E. O.; Lamb, A. J.; Brown, R. C. D., Convenient One-Pot Synthesis of Chromone Derivatives and Their Antifungal and Antibacterial Evaluation. Synthetic Communications, 2013, 43, 1549. 5. Abdel Ghani, S. B.; Weaver, L.; Zidan, Z. H.; Ali, H. M.; Keevil, C. W.; Brown, R. C. D., Microwave-assisted synthesis and antimicrobial activities of flavonoid derivatives. Bioorganic & Medicinal Chemistry Letters, 2008, 18, 518.

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Discussion: