3CLpro-1 References

3CLpro-1
Clinical data
Trade names	3CLpro-1
Legal status
Legal status	US: Investigational drug;
Identifiers
	IUPAC name (2S)-2-[[(E)-3-(4-chloro-2-fluorophenyl)prop-2-enoyl]amino]-N-[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-3-phenylpropanamide;
CAS Number	2409054-43-7;
PubChem CID	44578386;
ChemSpider	24697352;
ChEMBL	ChEMBL477164;
Chemical and physical data
Formula	C25H25ClFN3O4
Molar mass	485.94 g·mol−1
3D model ( JSmol)	Interactive image;
	SMILES C1CNC(=O)[C@@H]1C[C@@H](C=O)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)/C=C/C3=C(C=C(C=C3)Cl)F;
	InChI InChI=1S/C25H25ClFN3O4/c26-19-8-6-17(21(27)14-19)7-9-23(32)30-22(12-16-4-2-1-3-5-16)25(34)29-20(15-31)13-18-10-11-28-24(18)33/h1-9,14-15,18,20,22H,10-13H2,(H,28,33)(H,29,34)(H,30,32)/b9-7+/t18-,20-,22-/m0/s1; Key:HXAHMXYAYHWWRI-ZCTWNQIISA-N;

3CLpro-1 is an antiviral drug related to rupintrivir which acts as a 3CL protease inhibitor and was originally developed for the treatment of human enterovirus 71. It is one of the most potent of a large series of compounds developed as inhibitors of the viral enzyme 3CL protease, with an in vitro IC₅₀ of 200 nM. It also shows activity against coronavirus diseases such as SARS and MERS, and is under investigation as a potential treatment agent for the viral disease COVID-19.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

References

^ Kuo CJ, Shie JJ, Fang JM, Yen GR, Hsu JT, Liu HG, et al. (August 2008). "Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents". Bioorganic & Medicinal Chemistry. 16 (15): 7388–98. doi: 10.1016/j.bmc.2008.06.015. PMC 7125518. PMID 18583140.
^ Zhou Y, Vedantham P, Lu K, Agudelo J, Carrion R, Nunneley JW, et al. (April 2015). "Protease inhibitors targeting coronavirus and filovirus entry". Antiviral Research. 116: 76–84. doi: 10.1016/j.antiviral.2015.01.011. PMC 4774534. PMID 25666761.
^ Kumar V, Shin JS, Shie JJ, Ku KB, Kim C, Go YY, et al. (May 2017). "Identification and Evaluation of Potent Middle East Respiratory Syndrome Coronavirus (MERS-CoV) 3CL Pro Inhibitors". Antiviral Research. 141: 101–106. doi: 10.1016/j.antiviral.2017.02.007. PMC 7113684. PMID 28216367.
^ Liu C, Zhou Q, Li Y, Garner LV, Watkins SP, Carter LJ, et al. (2020). "Research and Development on Therapeutic Agents and Vaccines for COVID-19 and Related Human Coronavirus Diseases". ACS Central Science. 6 (3): 315–331. doi: 10.1021/acscentsci.0c00272. PMC 7094090. PMID 32226821.
^ Morse JS, Lalonde T, Xu S, Liu WR (March 2020). "Learning from the Past: Possible Urgent Prevention and Treatment Options for Severe Acute Respiratory Infections Caused by 2019-nCoV". ChemBioChem. 21 (5): 730–738. doi: 10.1002/cbic.202000047. PMC 7162020. PMID 32022370.
^ Zhang L, Lin D, Kusov Y, Nian Y, Ma Q, Wang J, et al. (February 2020). "α-Ketoamides as Broad-Spectrum Inhibitors of Coronavirus and Enterovirus Replication: Structure-Based Design, Synthesis, and Activity Assessment". Journal of Medicinal Chemistry. 63 (9): 4562–4578. doi: 10.1021/acs.jmedchem.9b01828. PMC 7098070. PMID 32045235.
^ Zhang L, Lin D, Sun X, Curth U, Drosten C, Sauerhering L, et al. (March 2020). "Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors". Science. 368 (6489): 409–412. Bibcode: 2020Sci...368..409Z. doi: 10.1126/science.abb3405. PMC 7164518. PMID 32198291.

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[1] Kuo CJ, Shie JJ, Fang JM, Yen GR, Hsu JT, Liu HG, et al. (August 2008). "Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents". Bioorganic & Medicinal Chemistry. 16 (15): 7388–98. doi: 10.1016/j.bmc.2008.06.015. PMC 7125518. PMID 18583140.

[2] Zhou Y, Vedantham P, Lu K, Agudelo J, Carrion R, Nunneley JW, et al. (April 2015). "Protease inhibitors targeting coronavirus and filovirus entry". Antiviral Research. 116: 76–84. doi: 10.1016/j.antiviral.2015.01.011. PMC 4774534. PMID 25666761.

[3] Kumar V, Shin JS, Shie JJ, Ku KB, Kim C, Go YY, et al. (May 2017). "Identification and Evaluation of Potent Middle East Respiratory Syndrome Coronavirus (MERS-CoV) 3CL Pro Inhibitors". Antiviral Research. 141: 101–106. doi: 10.1016/j.antiviral.2017.02.007. PMC 7113684. PMID 28216367.

[4] Liu C, Zhou Q, Li Y, Garner LV, Watkins SP, Carter LJ, et al. (2020). "Research and Development on Therapeutic Agents and Vaccines for COVID-19 and Related Human Coronavirus Diseases". ACS Central Science. 6 (3): 315–331. doi: 10.1021/acscentsci.0c00272. PMC 7094090. PMID 32226821.

[pmid32022370-5] Morse JS, Lalonde T, Xu S, Liu WR (March 2020). "Learning from the Past: Possible Urgent Prevention and Treatment Options for Severe Acute Respiratory Infections Caused by 2019-nCoV". ChemBioChem. 21 (5): 730–738. doi: 10.1002/cbic.202000047. PMC 7162020. PMID 32022370.

[6] Zhang L, Lin D, Kusov Y, Nian Y, Ma Q, Wang J, et al. (February 2020). "α-Ketoamides as Broad-Spectrum Inhibitors of Coronavirus and Enterovirus Replication: Structure-Based Design, Synthesis, and Activity Assessment". Journal of Medicinal Chemistry. 63 (9): 4562–4578. doi: 10.1021/acs.jmedchem.9b01828. PMC 7098070. PMID 32045235.

[7] Zhang L, Lin D, Sun X, Curth U, Drosten C, Sauerhering L, et al. (March 2020). "Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors". Science. 368 (6489): 409–412. Bibcode: 2020Sci...368..409Z. doi: 10.1126/science.abb3405. PMC 7164518. PMID 32198291.

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See also

References