Supplemental Table 1. Information About Leading Hit Antiviral Compounds

Supplemental Table 1. Information about leading hit antiviral compounds

Manuscript name / Library code / Substance code / Molecular Formula / Molecular Weight (g/mol) / IUPAC
1 / IBS000870 / STOCK2S-84507 / C17H19N3O3 / 313.35106 / (Z)-N'-(morpholin-4-carbonyloxy)-2-(naphthalen-1-yl) acetimidamide
2 / CBI001174 / A3104/0131463 / C9H12N2O5S / 260.26698 / 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
3 / IBS001602 / STOCK1S-27032 / C17H16Cl2N2O4S / 415.29094 / 2-methoxyethyl N-[[3-chloro-4-(4-chlorophenoxy)phenyl]carbamothioyl]carbamate
4 / CBI001247 / A3280/0139568 / C22H24O4 / 352.42356 / 4-(6-hydroxyspiro[1,2,3,9a-tetrahydrocyclopenta[b]chromene-9,1'-cyclopentane]-3a-yl)
benzene-1,3-diol

Supplemental Table 2. Information about a library of 69 compounds with similar structure of compound 1 used for SAR analysis

Manuscript name / Library code / Substance code / Molecular Formula / Molecular Weight (g/mol) / IUPAC
IBS003070 / STOCK2S-46290 / C17H14N2O2S / 310.37 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] thiophene-2-carboxylate
IBS003578 / STOCK2S-97670 / C17H15ClN2O2 / 314.77 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] (E)-3-phenylprop-2-enoate
IBS004609 / STOCK3S-97065 / C17H16Cl2N2O4 / 383.23 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 3,4-dimethoxybenzoate
8 / IBS004666 / STOCK4S-04046 / C12H14BrN3O3 / 328.16 / [(Z)-[amino-(4-bromophenyl)methylidene]amino] morpholine-4-carboxylate
IBS009650 / STOCK2S-43426 / C15H11ClN4O6 / 378.72 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 4-chloro-3-nitrobenzoate
IBS010650 / STOCK3S-11712 / C14H14N2O4 / 274.27 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] furan-2-carboxylate
IBS014606 / STOCK2S-98507 / C21H20N2O2 / 332.40 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 3-phenylpropanoate
IBS015507 / STOCK3S-01914 / C22H20N2O3 / 360.41 / [(Z)-[1-amino-2-(4-methoxyphenyl)ethylidene]amino] 4-phenylbenzoate
6 / IBS016939 / STOCK2S-86650 / C24H24N2O4 / 404.46 / [(Z)-[1-amino-2-(3,4-dimethoxyphenyl)ethylidene]amino] 2,2-diphenylacetate
IBS017170 / STOCK2S-49851 / C16H14Cl2N2O3 / 353.20 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 4-methoxybenzoate
5 / IBS017171 / STOCK2S-78117 / C17H17N3O6 / 359.33 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2,4-dimethoxybenzoate
IBS017172 / STOCK2S-63730 / C17H17N3O6 / 359.33 / [(Z)-[1-amino-2-(3,4-dimethoxyphenyl)ethylidene]amino] 2-nitrobenzoate
IBS017173 / STOCK2S-51104 / C19H15ClN2O2 / 338.79 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] naphthalene-1-carboxylate
IBS017174 / STOCK2S-51286 / C17H17N3O5 / 343.33 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino]4-methyl-3-nitrobenzoate
IBS017176 / STOCK2S-57898 / C19H15BrN2O2 / 383.24 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 2-bromobenzoate
IBS017177 / STOCK2S-62791 / C19H15BrN2O2 / 383.24 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 3-bromobenzoate
IBS017178 / STOCK2S-34941 / C19H15IN2O2 / 430.24 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 3-iodobenzoate
IBS017186 / STOCK3S-26536 / C15H12Cl2N2O2 / 323.17 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] benzoate
IBS017187 / STOCK3S-20291 / C19H21ClN2O2 / 344.84 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] 4-tert-butylbenzoate
IBS017188 / STOCK3S-23927 / C20H24N2O3 / 340.42 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] 4-tert-butylbenzoate
IBS017189 / STOCK3S-19335 / C16H15BrN2O3 / 363.21 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] 3-bromobenzoate
IBS017190 / STOCK2S-92401 / C15H12IN3O4 / 425.18 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-iodobenzoate
IBS017191 / STOCK2S-86859 / C15H12IN3O4 / 425.18 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 4-iodobenzoate
IBS017192 / STOCK2S-85134 / C13H10Cl2N2O2S / 329.20 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] thiophene-2-carboxylate
IBS017193 / STOCK3S-15176 / C16H13Cl3N2O2 / 371.65 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 2-(4-chlorophenyl)acetate
IBS017195 / STOCK3S-23951 / C17H17N3O5 / 343.33 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-(4-methoxyphenyl)acetate
IBS017196 / STOCK2S-98853 / C17H17N3O4 / 327.33 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 3-phenylpropanoate
IBS017197 / STOCK3S-02267 / C17H16Cl2N2O3 / 367.23 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 2-(2-methylphenoxy)acetate
IBS017198 / STOCK3S-18571 / C18H20N2O4 / 328.36 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] 2-(3-methylphenoxy)acetate
IBS017199 / STOCK3S-17741 / C17H16Cl2N2O3 / 367.23 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 2-(3-methylphenoxy)acetate
IBS017200 / STOCK2S-94903 / C17H17ClN2O3 / 332.78 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] 2-(4-methylphenoxy)acetate
IBS017201 / STOCK3S-20697 / C19H21BrN2O5 / 437.28 / [(Z)-[1-amino-2-(3,4-dimethoxyphenyl)ethylidene]amino] 2-(4-bromo-3-methylphenoxy)acetate
IBS017202 / STOCK3S-14303 / C17H17ClN2O4 / 348.78 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] 2-(4-methoxyphenoxy)acetate
IBS017204 / STOCK3S-08714 / C19H15ClN2O2 / 338.79 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] naphthalene-2-carboxylatez
IBS017205 / STOCK3S-25968 / C16H13Cl3N2O2 / 371.65 / [(Z)-[1-amino-2-(3,4-dichlorophenyl)ethylidene]amino] 2-chloro-4-methylbenzoate
IBS017206 / STOCK3S-14248 / C16H13Cl3N2O2 / 371.65 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 3-chloro-4-methylbenzoate
IBS017207 / STOCK3S-06620 / C16H14Cl2N2O3 / 353.20 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] 2-(2-chlorophenoxy)acetate
IBS017208 / STOCK2S-96571 / C15H11ClN4O6 / 378.72 / [(Z)-[1-amino-2-(4-chlorophenyl)ethylidene]amino] 3,5-dinitrobenzoate
IBS017209 / STOCK2S-86957 / C18H18N2O3 / 310.35 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] (E)-3-phenylprop-2-enoate
IBS017210 / STOCK3S-00413 / C17H17N3O5 / 343.33 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] 2-methyl-3-nitrobenzoate
IBS017211 / STOCK3S-21693 / C22H22N2O5 / 394.42 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 3,4,5-trimethoxybenzoate
IBS017212 / STOCK3S-21757 / C18H19N3O7 / 389.36 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 3,4,5-trimethoxybenzoate
IBS017213 / STOCK3S-28508 / C22H22N2O5 / 394.42 / [(Z)-[1-amino-2-(3,4-dimethoxyphenyl)ethylidene]amino] 2-naphthalen-2-yloxyacetate
IBS017214 / STOCK3S-18479 / C19H20Cl2N2O5 / 427.28 / [(Z)-[1-amino-2-(3,4-dimethoxyphenyl)ethylidene]amino] 2-(2,4-dichlorophenoxy)propanoate
IBS017215 / STOCK3S-14602 / C17H16ClN3O5 / 377.78 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-(4-chloro-3-methylphenoxy)acetate
IBS017216 / STOCK3S-07800 / C16H13BrClN3O5 / 442.65 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-(4-bromo-2-chlorophenoxy)acetate
IBS017217 / STOCK3S-04308 / C18H19N3O4 / 341.36 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 4-phenylbutanoate
IBS017219 / STOCK3S-08196 / C19H21N3O5 / 371.39 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-(4-propan-2-ylphenoxy)acetate
IBS017220 / STOCK2S-95483 / C22H22N2O3 / 362.42 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 2-(3,4-dimethylphenoxy)acetate
IBS017221 / STOCK3S-17659 / C18H19N3O5 / 357.36 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-(3,4-dimethylphenoxy)acetate
IBS017222 / STOCK2S-98772 / C18H18Cl2N2O3 / 381.25 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 2-(3,4-dimethylphenoxy)acetate
IBS017223 / STOCK2S-92409 / C15H11Cl3N2O2 / 357.62 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 3-chlorobenzoate
IBS017224 / STOCK3S-13614 / C16H15BrN2O3 / 363.21 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] 4-bromobenzoate
IBS017225 / STOCK2S-87812 / C16H15N3O5 / 329.31 / [(Z)-[1-amino-2-(4-methoxyphenyl)ethylidene]amino] 3-nitrobenzoate
IBS017226 / STOCK3S-20419 / C18H19N3O5 / 357.36 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-(3,5-dimethylphenoxy)acetate
IBS017228 / STOCK3S-06008 / C16H14ClN3O4 / 347.75 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 2-chloro-4-methylbenzoate
7 / IBS017229 / STOCK2S-99762 / C16H13Cl2N3O4 / 382.20 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 2-methyl-3-nitrobenzoate
IBS017230 / STOCK2S-93542 / C21H20N2O4 / 364.39 / [(Z)-[1-amino-2-(2-methoxyphenyl)ethylidene]amino] 2-naphthalen-1-yloxyacetate
IBS017231 / STOCK2S-94418 / C19H22N2O4 / 342.39 / [(Z)-[1-amino-2-(4-methoxyphenyl)ethylidene]amino] 2-(3,4-dimethylphenoxy)acetate
IBS017272 / STOCK2S-99262 / C20H17ClN2O3 / 368.81 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 2-(2-chlorophenoxy)acetate
IBS017273 / STOCK4S-07291 / C16H14Cl2N2O2 / 337.20 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 4-methylbenzoate
IBS017274 / STOCK4S-07860 / C15H11Cl2FN2O2 / 341.16 / [(Z)-[1-amino-2-(2,4-dichlorophenyl)ethylidene]amino] 2-fluorobenzoate
IBS017275 / STOCK4S-19176 / C15H12ClN3O4 / 333.73 / [(Z)-[1-amino-2-(4-nitrophenyl)ethylidene]amino] 4-chlorobenzoate
IBS017276 / STOCK3S-99469 / C21H20N2O4 / 364.39 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 3,4-dimethoxybenzoate
IBS017277 / STOCK4S-10875 / C19H15N3O4 / 349.34 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 4-nitrobenzoate
IBS017278 / STOCK4S-13653 / C15H11Cl2N3O4 / 368.17 / [(Z)-[1-amino-2-(3,4-dichlorophenyl)ethylidene]amino] 4-nitrobenzoate
IBS017279 / STOCK4S-25669 / C16H13Cl2N3O5 / 398.20 / [(Z)-[1-amino-2-(3,4-dichlorophenyl)ethylidene]amino] 4-methoxy-3-nitrobenzoate
IBS017280 / STOCK4S-08759 / C13H9BrCl2N2O3 / 392.03 / [(Z)-[1-amino-2-(3,4-dichlorophenyl)ethylidene]amino] 5-bromofuran-2-carboxylate
IBS017281 / STOCK4S-12402 / C20H17ClN2O3 / 368.81 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 5-chloro-2-methoxybenzoate

Supplemental Table 3. Information about compounds with N- (morpholine-4-carbonyloxy) amidine or with N-acyloxy-1-naphthalenacetamidine used for SAR analysis

Manuscript name / Substance code / Supplier / Molecular Formula / Molecular Weight (g/mol) / IUPAC
9 / STK873432 / Vitas-M / C12H15N3O3 / 249.27 / [(Z)-[amino(phenyl)methylidene]amino] morpholine-4-carboxylate
10 / BA 06107773 / Asinex / C13H17N3O3 / 263.29 / [(Z)-[amino-(3-methylphenyl)methylidene]amino] morpholine-4-carboxylate
11 / BAS06107776 / Asinex / C13H17N3O4 / 279.29 / [(Z)-[amino-(4-methylphenyl)methylidene]amino] morpholine-4-carboxylate
12 / SPB07191 / Maybridge / C12H14ClN3O3 / 283.71 / [(Z)-[amino-(4-chlorophenyl)methylidene]amino] morpholine-4-carboxylate
13 / 7986970 / ChemBridge / C12H14IN3O3 / 375.16 / [(Z)-[amino-(4-iodophenyl)methylidene]amino] morpholine-4-carboxylate
14 / SPB07194 / Maybridge / C12H13Cl2N3O3 / 318.16 / [(Z)-[amino-(2,6-dichlorophenyl)methylidene]amino]morpholine-4-carboxylate
15 / STK111170 / Vitas-M / C11H14N4O3 / 250.25 / [(Z)-[amino(pyridin-3-yl)methylidene]amino] morpholine-4-carboxylate
16 / STK111593 / Vitas-M / C11H14N4O3 / 250.25 / [(Z)-[amino(pyridin-2-yl)methylidene]amino] morpholine-4-carboxylate
17 / BAS06107776 / Asinex / C12H17N3O4 / 279.29 / [(Z)-[amino-(4-methoxyphenyl)methylidene]amino] morpholine-4-carboxylate
18 / BAS 06107777 / Asinex / C14H19N3O5 / 309.32 / [(Z)-[amino(3,4-dimethoxyphenyl)methylidene]amino] morpholine-4-carboxylate
19 / SPB07193 / Maybridge / C13H14F3N3O3 / 317.26 / [(Z)-[amino-[3-(trifluoromethyl)phenyl]methylidene]amino] morpholine-4-carboxylate
20 / STK185648 / Vitas-M / C12H14N4O5 / 294.26 / [(Z)-[amino-(4-nitrophenyl)methylidene]amino] morpholine-4-carboxylate
21 / 5215-0126 / ChemDiv / C14H16N4O5 / 308.29 / [(Z)-(1-amino-2-(4-nitrophenyl)ethylidene)amino] morpholine-4-carboxylate
22 / Z-020432 / ScientificExchange / C19H22N2O2 / 310.39 / (Z)-N'-((cyclohexanecarbonyl)oxy)-2-(naphthalen-1-yl)acetimidamide
23 / R-078205 / ScientificExchange / C17H14N2O3 / 294.30 / (Z)-N'-((furan-2-carbonyl)oxy)-2-(naphthalen-1-yl)acetimidamide
24 / SPB00827 / Maybridge / C19H16N2O2 / 304.34 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] benzoate
25 / STK323487 / Vitas-M / C20H18N2O2 / 318.37 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 4-methylbenzoate
26 / STK323491 / Vitas-M / C19H15FN2O2 / 322.33 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 2-fluorobenzoate
27 / STK043029 / Vitas-M / C20H18N2O3 / 334.37 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 2-methoxybenzoate
28 / STK140326 / Vitas-M / C20H18N2O3 / 334.37 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 3-methoxybenzoate
29 / STK105751 / Vitas-M / C20H17N3O4 / 363.37 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 2-methyl-3-nitrobenzoate
30 / STK068405 / Vitas-M / C20H17N3O4 / 363.37 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] 4-methyl-3-nitrobenzoate
31 / STK323559 / Vitas-M / C20H16N2O4 / 348.35 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino]1,3-benzodioxole-5-carboxylate
32 / STK028340 / Vitas-M / C25H19N3O2S / 425.50 / [(Z)-(1-amino-2-naphthalen-1-ylethylidene)amino] phenothiazine-10-carboxylate
33 / T5568723 / Enamine / C7H10F3NO3 / 213.15 / 2.2.2-trifluoroethyl morpholine-4-carboxylate
34 / 2454 / Ramidus AB / C6H11NO3 / 145.16 / methyl morpholine-4-carboxylate
35 / S349429 / SALOR / C7H13NO3 / 159.18 / ethyl morpholine-4-carboxylate