Indinavir CAS#: 150378-17-9; 凯望编码 (ChemWhat Code): 122584

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名Indinavir
IUPAC Name(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl]-N–tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
分子结构Indinavir-CAS-150378-17-9
CAS编号 150378-17-9
NACRESNA.77
别名Crixivan hydrate, L-735,524 hydrate, MK-639 hydrate, indinavir, Indinavir, (1(1S,2R),5(S))-2,3,5-trideoxy-N-(2,3-dihydro-2-hydroxy-1H-inden-1-yl)-5-(2-(((1,1-dimethylethyl)amino)carbonyl)-4-(3-pyridinylmethyl)-1-piperazinyl)-2-(phenylmethyl)-D-erythro-pentonamide, (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-5-oxopentyl]-N-(2-methyl-2-propanyl)-4-(3-pyridinylmethyl)-2-piperazinecarboxamide, (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide, (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3 ylrnethyl)piperazine-2-carboxarnide, (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-l-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
分子式C36H47N5O4
分子量613.8
InChIInChI=1S/C36H47N5O4/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45)/t28-,29+,31+,32-,33+/m1/s1
InChI KeyCBVCZFGXHXORBI-PXQQMZJSSA-N
Canonical SMILESCC(C)(C)NC(=O)C1CN(CCN1CC(CC(CC2=CC=CC=C2)C(=O)NC3C(CC4=CC=CC=C34)O)O)CC5=CN=CC=C5
Patent Information
Patent IDTitlePublication Date
US2011/245283Methods for predicting the response to statins2011
US2004/116692Reductive alkylation of saturated cyclic amines2004

Physical Data

AppearanceWhite to off-white powder
SolubilityH2O: ≥15 mg/mL
Melting Point, °C Solvent (Melting Point) Comment (Melting Point)
167.5 – 168ethyl acetateCrystallization with 0.65 Mol(s) H2O
Type (Optical Rotatory Power)Concentration (Optical Rotatory Power)Solvent (Optical Rotatory Power)Optical Rotatory Power, degWavelength (Optical Rotatory Power), nmTemperature (Optical Rotatory Power), °C
[alpha]0.0133 g/100mlCHCl324.158922
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Further physical properties of the complexaq. phosphate buffer, dimethylsulfoxide371,2-dioleoyl-sn-glycero-3-phosphoethanolamine, 1,2-Dioleoylphosphatidylserine, dioleoylphosphatidylcholine
Further physical properties of the complexaq. phosphate buffer, dimethylsulfoxide372-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine
IR spectrum of the complexCHCl3acrylic acid

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Original Text (NMR Spectroscopy)
Chemical shifts1HCDCl3
1H, 13Cchloroform-d11H NMR (400 MHz, CDCl3) δ 8.53 (dd J=1.6), 8.52 (d, J=2.0), 7.68 (bs), 7.60 (d, J=7.9, 2.0), 7.29 (m), 7.23 (m), 1.18-7.09 (m), 6.19 (d, J=8.5), 5.27 (dd, J=8.5, 4.8), 4.27 (m), 3.92 (br s), 3.81 (m), 3.49 (s), 3.12 (t, J=3.6), 3.02 (dd, J=16.7, 5.2), 2.98-2.47 (m), 2.34 (br s), 1.97, 1.56 (m), 1.50 (br s), 1.34 (s). 13C NMR (100 MHz, CDCl3) δ 175.0, 169.4, 151, 149, 140.4, 140.3, 139.9, 137, 133, 129.1, 128.5, 127.9 126.7, 123.9, 126.5, 125.1 123.4, 73.0, 65.8, 64.1, 61.4, 60, 57.4, 54.6, 52.7, 51.1, 47.9, 46.5, 39.6, 39.1, 38.1, 29.0.
Chemical shifts13CCDCl3
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
BandsCHCl33019 – 1366 cm**(-1)
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
SpectrummethanolRemark: first derivative spectrum, concentration dependence
methanolRemark: first derivative spectrum2739.284

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Indinavir CAS 150378-17-9
ConditionsYield
With methanol; hydrogen; platinum(IV) oxide In tetrahydrofuran for 3h;

Experimental Procedure
PtO2 (87 mg, 0.38 mmol) was added to the organic solution containing indinavir and its borane complex, whereupon the red-brown oxide immediately converted to very fine platinum black. Methanol (10 mL) was added and a mild evolution of hydrogen occurred over a period of about one hour. The batch was aged an additional two hours, whereupon HPLC analysis showed cleavage of the borane complex to be complete. The batch was then concentrated to remove THF, methanol and trimethoxyborate, and the concentrated batch was then diluted with isopropyl acetate. The batch was heated to 70° C., saturated with water and allowed to slowly cool to 0-5° C. to promote crystallization. The product was removed by filtration and washed with isopropyl acetate. Yield of 1=2.16 g, 92percent at a purity of 100percent by HPLC. 1H NMR (400 MHz, CDCl3) δ 8.53 (dd J=1.6), 8.52 (d, J=2.0), 7.68 (bs), 7.60 (d, J=7.9, 2.0), 7.29 (m), 7.23 (m), 1.18-7.09 (m), 6.19 (d, J=8.5), 5.27 (dd, J=8.5, 4.8), 4.27 (m), 3.92 (br s), 3.81 (m), 3.49 (s), 3.12 (t, J=3.6), 3.02 (dd, J=16.7, 5.2), 2.98-2.47 (m), 2.34 (br s), 1.97, 1.56 (m), 1.50 (br s), 1.34 (s). 13C NMR (100 MHz, CDCl3) δ 175.0, 169.4, 151, 149, 140.4, 140.3, 139.9, 137, 133, 129.1, 128.5, 127.9 126.7, 123.9, 126.5, 125.1 123.4, 73.0, 65.8, 64.1, 61.4, 60, 57.4, 54.6, 52.7, 51.1, 47.9, 46.5, 39.6, 39.1, 38.1, 29.0.		92%

Safety and Hazards

GHS Hazard StatementsNot Classified
Acute ToxicityLD50 Oral – Rat – > 5,000 mg/kg
LD50 Oral – Mouse – > 5,000 mg/kg
LD50 Oral – Dog – > 640 mg/kg
Remarks: Gastrointestinal disturbance
Inhalation: No data available
Dermal: No data available
LD50 Intraperitoneal – Rat – > 5,000 mg/kg
LD50 Intraperitoneal – Mouse – > 5,000 mg/kg
LD50 Intraperitoneal – Dog – > 640 mg/kg
Remarks: Gastrointestinal disturbance

Other Data

TransportationNot dangerous goods
Under room temperature and away from light
HS Code294200
StorageUnder 2-8°C away from light
Shelf Life1 year
Market Price
Use Pattern
Indinavir CAS#: 150378-17-9 may be used in HIV-related cell signaling studies.
Indinavir CAS#: 150378-17-9 is an antiviral HIV protease inhibitor.
Indinavir suppresses the replication of HIV and is an important component of antiretroviral therapy for initial treatment of HIV infection. It is known to cause renal and urologic toxicity.
reducing HIV- 1 reservoir in combination with antibody or a fragment that specifically binds to interferon-alpha/beta receptor to inhibit type I interferon signaling

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