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CAS No.: | 120279-96-1 |
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Name: | Dorzolamide |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C10H16N2O4S3 |
Molecular Weight: | 324.446 |
Synonyms: | Dorzolamide HCl;4H-Thieno[2,3-b]thiopyran-2-sulfonamide,4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-;4S,6S-Dorzolamide; |
EINECS: | 1533716-785-6 |
Density: | 1.53 g/cm3 |
Boiling Point: | 575.8 °C at 760 mmHg |
Flash Point: | 302 °C |
Appearance: | White or almost white crystalline powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26 |
(4S,6S)‑4‑acetamido‑5,6‑dihydro‑6‑methyl‑4H‑thieno[2,3‑b]thiopyran‑2‑sulfonamide‑7,7‑dioxide
dorzolamide
Conditions | Yield |
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With zinc(II) tetrahydroborate In methanol at 90℃; for 3h; Temperature; Solvent; Green chemistry; | 90% |
dorzolamide
Conditions | Yield |
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With hydrogenchloride; water In methanol for 72h; Heating / reflux; | 66% |
dorzolamide
Conditions | Yield |
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With dimethylsulfide borane complex; sulfuric acid 1) THF, r.t.; Yield given. Multistep reaction; |
(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one
dorzolamide
Conditions | Yield |
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Multi-step reaction with 7 steps 1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 3: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 4: 89.6 percent / H2SO4 / 20 - 25 °C 5: chlorosulfonic acid / 12 h / 50 °C 6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 7 steps 1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 3: H2SO4 / -5 °C 4: H2SO4 / -5 °C 5: chlorosulfonic acid / 12 h / 50 °C 6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 6 steps 1: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 2: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 3: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 4: chlorosulfonic acid / 12 h / 50 °C 5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
5,6-dihydro-(R)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran
dorzolamide
Conditions | Yield |
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Multi-step reaction with 6 steps 1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 2: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 3: 89.6 percent / H2SO4 / 20 - 25 °C 4: chlorosulfonic acid / 12 h / 50 °C 5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 6 steps 1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 2: H2SO4 / -5 °C 3: H2SO4 / -5 °C 4: chlorosulfonic acid / 12 h / 50 °C 5: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 6: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 5 steps 1: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 2: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 3: chlorosulfonic acid / 12 h / 50 °C 4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
(S)-3-(thien-2-ylthio)butyric acid
dorzolamide
Conditions | Yield |
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Multi-step reaction with 8 steps 1: trifluoroacetic anhydride / toluene / 1 h / 25 °C 2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 4: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 5: 89.6 percent / H2SO4 / 20 - 25 °C 6: chlorosulfonic acid / 12 h / 50 °C 7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 8 steps 1: trifluoroacetic anhydride / toluene / 1 h / 25 °C 2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 4: H2SO4 / -5 °C 5: H2SO4 / -5 °C 6: chlorosulfonic acid / 12 h / 50 °C 7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 7 steps 1: trifluoroacetic anhydride / toluene / 1 h / 25 °C 2: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 3: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 4: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 5: chlorosulfonic acid / 12 h / 50 °C 6: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 7: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
(S)-6-Methyl-6H-thieno[2,3-b]thiopyran 7,7-dioxide
dorzolamide
Conditions | Yield |
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Multi-step reaction with 4 steps 1: H2SO4 / -5 °C 2: chlorosulfonic acid / 12 h / 50 °C 3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
methyl (S)-3-(thiophen-2-ylthio)butyrate
dorzolamide
Conditions | Yield |
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Multi-step reaction with 9 steps 1: 45 g / 12 N HCl / H2O / 3 h / Heating 2: trifluoroacetic anhydride / toluene / 1 h / 25 °C 3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 5: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 6: 89.6 percent / H2SO4 / 20 - 25 °C 7: chlorosulfonic acid / 12 h / 50 °C 8: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 9: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 9 steps 1: 45 g / 12 N HCl / H2O / 3 h / Heating 2: trifluoroacetic anhydride / toluene / 1 h / 25 °C 3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 5: H2SO4 / -5 °C 6: H2SO4 / -5 °C 7: chlorosulfonic acid / 12 h / 50 °C 8: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 9: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 8 steps 1: 45 g / 12 N HCl / H2O / 3 h / Heating 2: trifluoroacetic anhydride / toluene / 1 h / 25 °C 3: LiAlH4 / tetrahydrofuran; toluene / 0 - 5 °C 4: 24 g / sodium tungstate dihydrate, 30 percent hydrogen peroxide / H2O; ethyl acetate; toluene / 1) 0 - 15 deg C, 30 min, 2) 25 deg C, 2 h 5: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 6: chlorosulfonic acid / 12 h / 50 °C 7: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 8: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
5,6-dihydro-(R,S)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide
dorzolamide
Conditions | Yield |
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Multi-step reaction with 5 steps 1: 95 percent / pyridine / tetrahydrofuran / 48 h / 25 - 30 °C 2: 89.6 percent / H2SO4 / 20 - 25 °C 3: chlorosulfonic acid / 12 h / 50 °C 4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 5 steps 1: H2SO4 / -5 °C 2: H2SO4 / -5 °C 3: chlorosulfonic acid / 12 h / 50 °C 4: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 5: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme | |
Multi-step reaction with 4 steps 1: 1) conc. H2SO4 / 1) THF, 48 h, r.t., 2) overnight 2: chlorosulfonic acid / 12 h / 50 °C 3: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 4: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
dorzolamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: conc. NH4OH / tetrahydrofuran / 1 h / 0 - 5 °C 2: 1) borane-dimethyl sulfide, 2) H2SO4 / 1) THF, r.t. View Scheme |
IUPAC Name: (4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[5,4-b]thiopyran-2-sulfonamide
Synonyms of Dorzolamide (CAS NO.120279-96-1) : 4S,6S-Dorzolamide ; 4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S,6S)- ; 4H-Thieno(2,3-b)thiopyran-2-sulfonamide, 4-(ethylamino)-5,6-dihydro-6-methyl-, 7,7-dioxide, (4S-trans)-
InChI: InChI=1/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1
CAS NO:120279-96-1
Molecular Formula:C10H16N2O4S3
Molecular Weight :324.44
Molecular Structure :
H bond acceptors: 6
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 119.76 Å2
Index of Refraction: 1.634
Molar Refractivity: 75.48 cm3
Molar Volume: 211 cm3
Surface Tension: 69.4 dyne/cm
Density: 1.53 g/cm3
Flash Point: 302 °C
Enthalpy of Vaporization: 86.23 kJ/mol
Boiling Point: 575.8 °C at 760 mmHg
Vapour Pressure: 2.93E-13 mmHg at 25°C
SMILES: O=S(=O)(c1sc2c(c1)C(NCC)CC(C)S2(=O)=O)N
InChI: InChI=1/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)
InChIKey: IAVUPMFITXYVAF-UHFFFAOYAE
Std. InChI: InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)
Std. InChIKey: IAVUPMFITXYVAF-UHFFFAOYSA-N
Dorzolamide (CAS NO.120279-96-1) is a carbonic anhydrase inhibitor. It is an anti-glaucoma agent and topically applied in the form of eye drops.