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Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02 Page 45 of 50

43 μM), and 16-hydroxy dehydroabietic acid (113) (IC = 81 ± 90 μM), showed potent α-glucosidase
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inhibitory activity. In addition, Compounds, oleanolic acid (117) (IC50 = 12.8 ± 0.00 μM), 2α, 3β, 11β-
trihydroxyolean-12-en-28-oic acid (118) (IC50 = 444.0 ± 8.0 μM), and 2α, 3β-dihydroxyolean-12-en-28-oic
acid (119) (IC50 = 666.0 ± 20.0 μM), showed significant α-glucosidase inhibitory activity, as compared to the
standard drug, acarbose (IC50 = 780.0 ± 0.28 μM). Compounds, 18-glycyrrhetinic acid (120) (IC = 225.1 ±
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0.5 μM), 3,7-dihydroxy-11-oxo-olean-12-en-30-oic acid (121) (IC ≥ 300 μM), and 3, 11-dioxo-olean-12-en-
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30-oic acid (122) (IC = 144.2 ± 0.2 μM), exhibited a good lipoxygenase (LOX) inhibitory activity, as
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compared to the standard drug, baicalein (IC = 22.4 ± 0.5 μM).
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Compounds, DHEA (143) (IC = 77.9 ± 1.95 μM), 3β,7α-dihydroandrost-5-ene-17-one (150) (IC = 373.5 ±
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9.57 μM), 11β-hydroxyandrost-4, 6-diene-3, 17-dione (152) (IC = 430 ± 7.13 μM), 5α-androstane-3, 17-
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dione (154)(IC = 221.6 ± 12.5 μM), and androst-4-ene-3, 17-dione (155) (IC = 191.4 ± 1.17 μM), showed
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significant activity against β-glucuronidase enzymes. Compounds 185 (IC = 190.3 ± 1.18 μM) and 187 (IC
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= 482.66 ± 6.86 μM) showed weak inhibition of β-glucuronidase. Derivative, 15α, 17β-dihydroxy-17α-
methylandrost-1, 4-dien-3-one (247) showed a remarkable β-glucuronidase inhibitory activity (IC = 60.7 μ
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M). Interestingly, derivative, 6β-hydroxy-etonogestrel (308), was found to be significantly active against β-
glucuronidase enzyme with the IC value of 13.97 ± 0.12 μM, compared to the standard inhibitor, D-
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saccharic acid 1, 4 lactone (IC = 48.4 ± 1.25 μM).
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Nandrolone (175) (IC = 32.0 ± 0.5 μM), and its derivatives, 10β, 12β, 17β-trihydroxy-19-nor-4-androsten-3-
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one (178) (IC ≥ 100 μM), 10β, 16α, 17β-trihydroxy-19-nor-4-androsten-3-one (179) (IC = 77.39 ± 5.52 μ
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M), 6β, 10β, 17β-trihydroxy-19-nor-4-androsten-3-one (180) (IC = 70.90 ± 1.16 μM), 10β, 17β-dihydroxy-
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19-nor-4-androsten-3-one (181) (IC = 54.94 ± 1.01 μM), 6β, 17β-dihydroxy-19-nor-4-androsten-3-one (
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182) (IC = 80.23 ± 3.39 μM), 10β-hydroxy-19-nor-4-androsten-3, 17-dione (183) (IC = 61.12 ± 1.39 μM),
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and 16β, 17β-dihydroxy-19-nor-4-androsten-3-one (184) (IC = 29.55 ± 1.14 μM) exhibited significant anti-
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leishmanial activity against Leishmania major in vitro.
Compounds, metenolone acetate (220) (62.5% ± 4.4 %), 6α-hydroxy-1-methyl-3-oxo-5α-androst-1-en-17-yl
acetate (221) (73.4% ± 0.6 %), 15β, 20-dihydroxy-1-methyl-3-oxo-5α-androst-1-en-17-yl acetate (224) (81.0%
± 2.5 %), 17β-hydroxy-1-methyl-3-oxo-5α-androst-1-en (227) (69.7% ± 1.4 %), 1-methyl-5β-androst-1-en-3,
17-dione (229) (73.2% ± 0.3%), 17β-hydroxy-1α-methyl-5α-androstan-3-one (232) (60.1% ± 3.3 %), and 17β,
15α-dihydroxy-1α-methyl-5α-androstan-3-one (233) (71.0% ± 7.2 %), showed good inhibition of cytokine
(TNF-α) production. Melengestrol acetate (352) (IC = 2.77 ± 0.08 µM), and its derivatives, 17α-acetoxy-11α
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-hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione (353) (IC = 2.78 ± 0.07 µM), 17α-acetoxy-6,
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7α-epoxy-6β-methyl-16-methylenepregna-4, 6-diene-3,20-dione (355) (IC = 2.74± 0.1 µM), and 17α-
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acetoxy-11β, 15β-dihydroxy-6-methyl-16-methylenepregna-4, 6-diene-3, 20-dione (356) (IC ≤ 2 µM),
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showed potent T- cell proliferation inhibitory activities. Similarly, medrysone (357) (IC = 2.0 ± 0.04 μg/
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mL), and its derivatives, 14α-hydroxy-6α-methylpregn-4-ene-3, 11, 20-trione (358) (IC = 20.0 ± 0.9 μg/mL),
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6β-hydroxy-6α-methylpregn-4-ene-3, 11, 20-trione (359) (IC = 14.6 ± 2.1 μg/mL), 15β-hydroxy-6α-
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methylpregn-4-ene-3, 11, 20-trione (360) (IC = 9.2 ± 0.7 μg/mL), 6β, 17α-dihydroxy-6α-methylpregn-4-
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ene-3, 11, 20-trione (361) (IC = 1.2 ± 0.02 μg/mL), 6β, 20(S)-dihydroxy-6α-methylpregn-4-ene-3, 11-dione
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(362) (IC = 15.2 ± 2.4 μg/mL), 11β, 16β-dihydroxy-6α-methylpregn-4-ene-3-one (363) (IC ≤ 0.2 μg/mL),
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and 15β, 20(R)-dihydroxy-6α-methylpregn-4-ene-3, 11-dione (364) (IC = 10.4 ± 0.42 μg/mL), also showed
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potent activities against T-cell proliferation in vitro, as compared to the standard drug, prednisolone (IC ≤
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3.1 μg/mL).