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thiophenol
(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide
A
nelfinavir
B
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In various solvent(s) at 115℃; for 4h; | A 84% B 8 % Chromat. |
With triethylamine In N,N-dimethyl-formamide at 80℃; for 10h; Product distribution; other base, other temperature, other solvents; | A 84 % Chromat. B 16 % Chromat. |
In ethylene glycol at 120℃; for 20h; | A 18 % Chromat. B 82 % Chromat. |
thiophenol
(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide
nelfinavir
Conditions | Yield |
---|---|
82% | |
With potassium hydrogencarbonate at 140℃; for 5h; Sealed tube; | 78% |
With potassium hydrogencarbonate In various solvent(s) Substitution; | 72% |
With triethylamine In water; N,N-dimethyl-formamide; toluene; butanone | 65% |
Conditions | Yield |
---|---|
Stage #1: 3-acetoxy-2-methylbenzoyl chloride; (2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate In ethanol Stage #2: With sodium hydroxide | 79% |
thiophenol
butanone
(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide
nelfinavir
Conditions | Yield |
---|---|
In pyridine | 69% |
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide
Acetic acid 3-((1R,2S)-2,3-dihydroxy-1-phenylsulfanylmethyl-propylcarbamoyl)-2-methyl-phenyl ester
nelfinavir
Conditions | Yield |
---|---|
Stage #1: Acetic acid 3-((1R,2S)-2,3-dihydroxy-1-phenylsulfanylmethyl-propylcarbamoyl)-2-methyl-phenyl ester With triethylamine; p-toluenesulfonyl chloride Stage #2: (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide | 59% |
nelfinavir
Conditions | Yield |
---|---|
With ammonia; water In methanol at 20℃; for 1.5h; | 54% |
With ammonia; water In methanol at 20℃; for 3h; Inert atmosphere; | 884 mg |
Stage #1: (3S,4AS,8AS)-2-[(2R,3R)-3-(3-acetoxy-2-methylbenzoylamino)-2-hydroxy-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic acid t-butylamide With sodium hydroxide; water; benzyl alcohol at 20 - 82℃; for 0.583333h; pH=14; Stage #2: With water; acetic acid In benzyl alcohol at 53℃; pH=7 - 7.5; Product distribution / selectivity; |
thiophenol
A
nelfinavir
B
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
Conditions | Yield |
---|---|
Stage #1: (2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-4-hydroxybutan-2-yl-4-methoxybenzoate With methanesulfonyl chloride; triethylamine In N,N-dimethyl-formamide at 20℃; Stage #2: thiophenol at 120℃; Stage #3: With potassium carbonate In methanol at 40℃; | A 31% B 41% |
3-acetoxy-2-methylbenzoic acid
nelfinavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 72 percent / EDCI; HOBt 2: 100 percent / HCl / methanol / 3 h / 40 °C 3: 59 percent / TsCl; Et3N View Scheme |
nelfinavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 72 percent / EDCI; HOBt 2: 100 percent / HCl / methanol / 3 h / 40 °C 3: 59 percent / TsCl; Et3N View Scheme |
nelfinavir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 71 percent / BF3*Et2O; NaI 2: 72 percent / EDCI; HOBt 3: 100 percent / HCl / methanol / 3 h / 40 °C 4: 59 percent / TsCl; Et3N View Scheme |
The Nelfinavir, with the CAS registry number 159989-64-7, is also known as 3-Isoquinolinecarboxamide,N-(1,1-dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-,(3S,4aS,8aS)-. This chemical's molecular formula is C32H45N3O4S and molecular weight is 567.79. What's more, its systematic name is (3S,4aS,8aS)-2-[(2R,3R)-2-Hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylsulfanyl)butyl]-N-(2-methyl-2-propanyl)decahydro-3-isoquinolinecarboxamide. Its classification codes are: (1)Anti-HIV agents; (2)Anti-Infective Agents; (3)Anti-Retroviral Agents; (4)Antiviral Agents; (5)Enzyme Inhibitors; (6)HIV Protease inhibitors; (7)Protease Inhibitors. This chemical is a potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. It belongs to the class of drugs known as protease inhibitors (PIs) and like other PIs is generally used in combination with other antiretroviral drugs.
Physical properties of Nelfinavir are: (1)ACD/LogP: 7.278; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 6.80; (4)ACD/LogD (pH 7.4): 7.26; (5)ACD/BCF (pH 5.5): 66657.38; (6)ACD/BCF (pH 7.4): 193716.50; (7)ACD/KOC (pH 5.5): 72239.41; (8)ACD/KOC (pH 7.4): 209938.70; (9)#H bond acceptors: 7; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 127.2 Å2; (13)Index of Refraction: 1.619; (14)Molar Refractivity: 162.378 cm3; (15)Molar Volume: 463.136 cm3; (16)Polarizability: 64.372×10-24cm3; (17)Surface Tension: 58.72 dyne/cm; (18)Density: 1.226 g/cm3; (19)Flash Point: 429.665 °C; (20)Enthalpy of Vaporization: 120.056 kJ/mol; (21)Boiling Point: 786.839 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1cccc(O)c1C)N[C@@H](CSc2ccccc2)[C@H](O)CN4[C@H](C(=O)NC(C)(C)C)C[C@@H]3CCCC[C@@H]3C4
(2)Std. InChI: InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1
(3)Std. InChIKey: QAGYKUNXZHXKMR-HKWSIXNMSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD | oral | > 5gm/kg (5000mg/kg) | Toxicologist. Vol. 42, Pg. 55, 1998. |