Cidofovir supplier | CasNO.113852-37-2

Name
Cidofovir
EINECS 638-807-0
CAS No. 113852-37-2
Article Data10
CAS DataBase
Density 1.76 g/cm³
Solubility
Melting Point 260 °C
Formula C₈H₁₄N₃O₆P
Boiling Point 609.5 °C at 760 mmHg
Molecular Weight 279.189
Flash Point 322.4 °C
Transport Information
Appearance fluffy white powder
Safety 36-37-45
Risk Codes 25-38
Molecular Structure
Hazard Symbols T
Synonyms Phosphonicacid, [[(1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]-(9CI);Phosphonic acid,[[2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]-, (S)-;(S)-1-(3-hydroxy-2-phosphonomethoxypropyl)cytosine;(S)-HPMPC;1-(S)-(3-Hydroxy-2-phosphonylmethoxypropyl)cytosine;1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine;Cidovir;GS 0504;HPMPC;Vistide;
PSA 157.71000
LogP -1.08060

Synthetic route

: 120362-35-8
(S)-1-<3-Hydroxy-2-<(diethylphosphonyl)methoxy>propyl>cytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With trimethylsilyl bromide In acetonitrile for 14h; Ambient temperature;	95%
With trimethylsilyl bromide	80%

: 132336-37-9
N4-benzoyl-1-(S)-(3-hydroxy-2-phosphonomethoxypropyl)cytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With ammonium hydroxide at 20℃; for 3h;	80%
With ammonium hydroxide for 4h; Ambient temperature; Yield given;

: C10H16N3O7P

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With ammonium hydroxide at 20℃; for 3h;	71%

: 18002-25-0
4-methoxy-2-pyrimidone

: 141110-74-9
(R)-2--3-ytimethylacetyl-1,2,3-propanetriol 1-p-toluenesulfonate

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 71-30-7
Cytosine

: 141110-74-9
(R)-2--3-ytimethylacetyl-1,2,3-propanetriol 1-p-toluenesulfonate

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With trimethylsilyl bromide; caesium carbonate 1.) DMFA, 100 deg C, 72 h, 2.) CH3CN, RT, 24 h; Yield given. Multistep reaction;

: 148873-52-3
bis(2-propyl) N4-benzoyl-1-(S)-(2-phosphonomethoxy-3-triphenylmethoxypropyl)cytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With trimethylsilyl bromide; sodium methylate 1.) CH3CN, overnight, 2.) CH3OH, RT, overnight; Yield given. Multistep reaction;

: 148873-53-4
bis(2-propyl) 1-(S)-(3-hydroxy-2-phosphonomethoxypropyl)cytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With trimethylsilyl bromide; water; triethylamine 1.) CH3CN, overnight, 2.) 20 min; Multistep reaction;

: 132336-34-6
(S)-N1-[2-hydroxy-3-(triphenylmethoxy)propyl]-N4-benzoylcytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylformamide / 6 h / 0 °C 2: HCl(g) / CH2Cl2 / 0.17 h / 0 - 5 °C 3: TMSBr / CH2Cl2 / 18 h / Ambient temperature 4: conc. NH4OH / 4 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 12 h / 60 °C 2: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 3: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 4: ammonium hydroxide / 3 h / 20 °C View Scheme

: 132336-36-8
diethyl (S)-4-N-benzoyl-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: TMSBr / CH2Cl2 / 18 h / Ambient temperature 2: conc. NH4OH / 4 h / Ambient temperature View Scheme

: 132336-35-7
[(S)-1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-trityloxy-ethoxymethyl]-phosphonic acid diethyl ester

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl(g) / CH2Cl2 / 0.17 h / 0 - 5 °C 2: TMSBr / CH2Cl2 / 18 h / Ambient temperature 3: conc. NH4OH / 4 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 2: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 3: ammonium hydroxide / 3 h / 20 °C View Scheme

: 120362-33-6
(S)-1-<3-(Benzyloxy)-2-<(diethylphosphonyl)methoxy>propyl>cytosine

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 12 h / Heating 2: 95 percent / Me3SiBr / acetonitrile / 14 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 65 percent / H2 / Pd(OH)2 on carbon / ethanol; cyclohexane / Heating 2: 80 percent / TMS-bromide View Scheme

: methyl (S)-2-((S)-2-amino-3-methyl-butyrylamino)-3-[(S)-5-(4-amino-2-oxo-2H-pyrimidin-1ylmethyl)-2-oxido-1,4,2-dioxaphosphinan-2-yloxy]propanoate

A: 1224569-63-4
Ser-cHPMPC

B: Val-Ser-HPMPC

C: 127757-45-3
cyclic cidofovir

D: 113852-37-2
cidofovir

Conditions

Conditions	Yield
With recombinant puromycin-sensitive aminopeptidase; sodium chloride In water at 37℃; pH=7.4; Kinetics; aq. buffer; Enzymatic reaction;

...Expand

: N-(2-oxo-1-(2-(trimethylsilyl)allyl)-1,2-dihydropyrimidin-4-yl)benzamide

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: methanesulfonamide; C50H56N4O4; potassium carbonate; potassium hexacyanoferrate(III); K2Os2(OH)4 / water; tert-butyl alcohol / 12 h / 0 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 0 °C / Inert atmosphere 3: dmap / dichloromethane 4: potassium carbonate / acetonitrile / 12 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 6: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 7: ammonium hydroxide / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: methanesulfonamide; C50H56N4O4; potassium carbonate; potassium hexacyanoferrate(III); K2Os2(OH)4 / water; tert-butyl alcohol / 12 h / 0 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 0 °C / Inert atmosphere
3: dmap / dichloromethane
4: potassium carbonate / acetonitrile / 12 h / 60 °C
5: trifluoroacetic acid / dichloromethane / 6 h / 20 °C
6: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C
7: ammonium hydroxide / 3 h / 20 °C
View Scheme

: C17H23N3O4Si

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 0 °C / Inert atmosphere 2: dmap / dichloromethane 3: potassium carbonate / acetonitrile / 12 h / 60 °C 4: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 5: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 6: ammonium hydroxide / 3 h / 20 °C View Scheme

: C9H13N3O4

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: dmap / dichloromethane 2: potassium carbonate / acetonitrile / 12 h / 60 °C 3: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 4: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 5: ammonium hydroxide / 3 h / 20 °C View Scheme

: C28H27N3O4

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 12 h / 60 °C 2: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 3: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 4: ammonium hydroxide / 3 h / 20 °C View Scheme

: C33H38N3O7P

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 2: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 3: ammonium hydroxide / 3 h / 20 °C View Scheme

: C14H24N3O7P

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 2: ammonium hydroxide / 3 h / 20 °C View Scheme

: 62853-19-4
(S)-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: dmap / dichloromethane 2: potassium carbonate / acetonitrile / 12 h / 60 °C 3: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 4: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 5: ammonium hydroxide / 3 h / 20 °C View Scheme

: 648881-65-6
N-(1-allyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

: 113852-37-2
cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: methanesulfonamide; C50H56N4O4; potassium carbonate; potassium hexacyanoferrate(III); K2Os2(OH)4 / water; tert-butyl alcohol / 12 h / 0 °C 2: dmap / dichloromethane 3: potassium carbonate / acetonitrile / 12 h / 60 °C 4: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 5: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C 6: ammonium hydroxide / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: methanesulfonamide; C50H56N4O4; potassium carbonate; potassium hexacyanoferrate(III); K2Os2(OH)4 / water; tert-butyl alcohol / 12 h / 0 °C
2: dmap / dichloromethane
3: potassium carbonate / acetonitrile / 12 h / 60 °C
4: trifluoroacetic acid / dichloromethane / 6 h / 20 °C
5: trimethylsilyl bromide / dichloromethane / 18 h / 20 °C
6: ammonium hydroxide / 3 h / 20 °C
View Scheme

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 113852-37-2
cidofovir

: 278611-17-9
(S)-1-{3-[4,4'-Dimethoxytrityloxy]-2-(phosphonomethoxy)propyl}cytosine

Conditions

Conditions	Yield
In dimethyl sulfoxide	95%
Stage #1: cidofovir With tributyl-amine In methanol Stage #2: 4,4'-dimethoxytrityl chloride With tributyl-amine In dimethyl sulfoxide at 20℃;	91%

: 113852-37-2
cidofovir

: 111-27-3
hexan-1-ol

: 1393360-99-0
C14H24N3O5P

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 24h; Inert atmosphere;	65%

: 112-53-8
1-dodecyl alcohol

: 113852-37-2
cidofovir

: 849176-91-6
dodecyl cyclic cidofovir

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; for 24h; Inert atmosphere;	62%

: 1393360-95-6
C22H41N3O3S

: 113852-37-2
cidofovir

: 1393360-98-9
C30H51N6O7PS

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; Inert atmosphere;	61%

: 113852-37-2
cidofovir

: 106451-92-7
6-N-Biotinylaminohexanol

: 1393360-97-8
C24H39N6O7PS

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; Inert atmosphere;	56%

: 95611-10-2
C12H21N3O3S

: 113852-37-2
cidofovir

: 1393360-96-7
C20H31N6O7PS

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃; Inert atmosphere;	45%

: 113852-37-2
cidofovir

: N,N-dicyclohexyl-4-morpholine carboxamidine

: cyclic cidofovir N,N-dicyclohexyl-4-morpholinocarboxamidine salt

Conditions

Conditions	Yield
Stage #1: cidofovir; N,N-dicyclohexyl-4-morpholine carboxamidine In N,N-dimethyl-formamide Stage #2: With pyridine; dicyclohexyl-carbodiimide at 60 - 100℃; for 16h;	44%
Stage #1: cidofovir; N,N-dicyclohexyl-4-morpholine carboxamidine In DMF (N,N-dimethyl-formamide) Stage #2: With pyridine; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at 60 - 100℃; for 16.5h;	44%
With dicyclohexyl-carbodiimide In pyridine; N,N-dimethyl-formamide at 20 - 100℃; for 28h;

: 4975-73-9
N,N'-dicyclohexyl-4-morpholine carboxamidine

: 113852-37-2
cidofovir

: 912635-37-1
cyclic cidofovir DCMC salt

Conditions

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃; for 16h;	44%
Stage #1: N,N'-dicyclohexyl-4-morpholine carboxamidine; cidofovir In N,N-dimethyl-formamide Stage #2: With pyridine; dicyclohexyl-carbodiimide at 60 - 100℃; for 16.5h;	44%

: 113852-37-2
cidofovir

: cidofovir monophosphate

Conditions

Conditions	Yield
With pyrimidine nucleoside monophosphate kinase (EC 2.7.4.14); ATP In phosphate buffer at 37℃; for 15h; pH=7.5; Enzyme kinetics; Further Variations:; Reaction partners; phosphorylation;

: 541-41-3
chloroformic acid ethyl ester

: 113852-37-2
cidofovir

: C14H22N3O10P

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 60 - 65℃; for 0.5h;

: 113852-37-2
cidofovir

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 127757-45-3
cyclic cidofovir

B: 1-(2-hydroxy-2-oxo-2λ5-[1,4,2]dioxaphosphinan-5-ylmethyl)-1H-pyrimidine-2,4-dione

C: N'-[1-(2-hydroxy-2-oxo-2λ5-[1,4,2]dioxaphosphinan-5-ylmethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethyl-formamidine

D: [2-{[2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-hydroxy-phosphinoyloxy}-1-(4-amino-2-oxo-2H-pyrimidin-1-ylmethyl)-ethoxymethyl]-phosphonic acid

Conditions

Conditions	Yield
With oxalyl dichloride Product distribution; Further Variations:; Reagents;

...Expand

: 4070-48-8
L-Valine methyl ester

: 113852-37-2
cidofovir

: C14H25N4O7P

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water

: 17431-03-7
L-valine ethyl ester

: 113852-37-2
cidofovir

: C15H27N4O7P

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water

: 113852-37-2
cidofovir

: 127757-45-3
cyclic cidofovir

Conditions

Conditions	Yield
With pyridine; N,N'-dicyclohexyl-4-morpholine carboxamidine; dicyclohexyl-carbodiimide at 100℃;
Multi-step reaction with 2 steps 1: EDC / H2O 2: PyBOP View Scheme
Multi-step reaction with 2 steps 1: dimethylformamide / 0.5 h / 60 - 65 °C 2: 94 percent / NaOH / H2O; dimethylformamide; methanol / pH 3.5 View Scheme
With methanol; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 35℃; for 3h;
With N,N'-dicyclohexyl-4-morpholine carboxamidine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃;

: 113852-37-2
cidofovir

: 6-Amino-3-((S)-3-hydroxy-2-phosphonomethoxy-propyl)-2-oxo-2,3,4,5-tetrahydro-pyrimidine-4-sulfonic acid

Conditions

Conditions	Yield
With triethylammonium hydrogensulfite; triethylamine In methanol at 20℃;

: 929207-84-1
(S)-2-hydroxyethyl 2-(tert-butoxycarbonylamino)-3-methylbutanoate

: 113852-37-2
cidofovir

: 2-tert-butoxycarbonylamino-3-methyl-butyric acid 2-[5-(4-amino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-oxo-2λ5-[1,4,2]dioxaphosphinan-2-yloxy]-ethyl ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃;

: 143184-61-6
2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-hydroxy-ethyl ester

: 113852-37-2
cidofovir

: 2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-[5-(4-amino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-oxo-2λ5-[1,4,2]dioxaphosphinan-2-yloxy]-ethyl ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃;

: 929207-84-1
(S)-2-hydroxyethyl 2-(tert-butoxycarbonylamino)-3-methylbutanoate

: 113852-37-2
cidofovir

: 76-05-1
trifluoroacetic acid

: 2-amino-3-methyl-butyric acid 2-[5-(4-amino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-oxo-2λ5-[1,4,2]dioxaphosphinan-2-yloxy]-ethyl ester; compound with trifluoro-acetic acid

Conditions

Conditions	Yield
Stage #1: (S)-2-hydroxyethyl 2-(tert-butoxycarbonylamino)-3-methylbutanoate; cidofovir With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; Stage #2: trifluoroacetic acid In dichloromethane at 20℃; for 3h;

...Expand

: 143184-61-6
2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-hydroxy-ethyl ester

: 113852-37-2
cidofovir

: 76-05-1
trifluoroacetic acid

: 2-amino-3-phenyl-propionic acid 2-[5-(4-amino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-oxo-2λ5-[1,4,2]dioxaphosphinan-2-yloxy]-ethyl ester; compound with trifluoro-acetic acid

Conditions

Conditions	Yield
Stage #1: 2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-hydroxy-ethyl ester; cidofovir With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; Stage #2: trifluoroacetic acid In dichloromethane at 20℃; for 3h;

...Expand

: 113852-37-2
cidofovir

: 1-[(S)-3-hydroxy-2-(phosphonomethoxy)propyl]-N4-cyclopropylcytosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylammonium hydrogensulfite; Et3N / aq. methanol / 20 °C 2: 1 g / aq. methanol / 16 h / 70 °C View Scheme

: 113852-37-2
cidofovir

: 343248-25-9
1-O-hexadecyloxypropyl cyclic cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dicyclohexyl-morpholinocarboxamidine; 1,3-dicyclohexylcarbodiimide; pyridine / 100 °C 2: dimethylformamide / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 1,3-dicyclohexyl carbodiimide / dimethylformamide; pyridine / 28 h / 20 - 100 °C 2: 31 percent / dimethylformamide / 6 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide 1.2: 16.5 h / 60 - 100 °C 2.1: N,N-dimethyl-formamide / 6 h / 80 °C View Scheme

: 113852-37-2
cidofovir

: 343248-29-3
1-O-octadecyloxyethyl cyclic cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dicyclohexyl-morpholinocarboxamidine; 1,3-dicyclohexylcarbodiimide; pyridine / 100 °C 2: dimethylformamide / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 1,3-dicyclohexyl carbodiimide / dimethylformamide; pyridine / 28 h / 20 - 100 °C 2: 33 percent / dimethylformamide / 6 h / 80 °C View Scheme

: 113852-37-2
cidofovir

: hexadecyloxypropyl-cidofovir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dicyclohexyl-morpholinocarboxamidine; 1,3-dicyclohexylcarbodiimide; pyridine / 100 °C 2: dimethylformamide / 80 °C 3: aq. NaOH View Scheme
Multi-step reaction with 3 steps 1: 1,3-dicyclohexyl carbodiimide / dimethylformamide; pyridine / 28 h / 20 - 100 °C 2: 31 percent / dimethylformamide / 6 h / 80 °C 3: 105 mg / aqueous NaOH / 1.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide 1.2: 16.5 h / 60 - 100 °C 2.1: N,N-dimethyl-formamide / 6 h / 80 °C 3.1: sodium hydroxide / 1.5 h / 20 °C 3.2: 3 h / 20 °C / pH 3.51 View Scheme

Cidofovir Analytical Methods

Antineoplastic Agents : substances that inhibit or prevent the proliferation of NEOPLASMS

Cidofovir Specification

The Phosphonic acid,P-[[(1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]-, with the CAS registry number 113852-37-2, is also known as 1-(S)-(3-Hydroxy-2-phosphonylmethoxypropyl)cytosine. This chemical's molecular formula is C₈H₁₄N₃O₆P and molecular weight is 279.19. What's more, its systematic name is ({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid. Its classification codes are: (1)Anti-HIV agents; (2)Anti-Infective Agents; (3)Anti-Retroviral Agents; (4)Antineoplastic Agents; (5)Antiviral; (6)Antiviral agents; (7)Radiation-Sensitizing Agents. It is a potent, selective inhibitor of human cytomegalovirus replication. It is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS.

Physical properties of Phosphonic acid,P-[[(1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]- are: (1)ACD/LogP: -3.37; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -6.65; (4)ACD/LogD (pH 7.4): -7.31; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 9; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 99.71 Å²; (13)Index of Refraction: 1.656; (14)Molar Refractivity: 58.29 cm³; (15)Molar Volume: 158.6 cm³; (16)Polarizability: 23.1×10^-24cm³; (17)Surface Tension: 90.5 dyne/cm; (18)Density: 1.76 g/cm³; (19)Flash Point: 322.4 °C; (20)Enthalpy of Vaporization: 103.84 kJ/mol; (21)Boiling Point: 609.5 °C at 760 mmHg; (22)Vapour Pressure: 2.11E-17 mmHg at 25°C.

Preparation: first dissolving 1-(2, 3-dihydroxypropyl)cytosine in triethyl phosphate, then adding in ClCH₂P(O)Cl₂ by stiring, and then mixing and rejoining the ether, filtering and collecting the precipitates which are washed with ether and then dried in the vacuum. Then dissolving the intermediate product in water and conducting backflow which is then neutralized with triethylamine and evaporated out solvent in the vacuum. Finally by column chromatography, the product is prepared.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1/N=C(\C=C/N1C[C@H](OCP(=O)(O)O)CO)N
(2)Std. InChI: InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1
(3)Std. InChIKey: VWFCHDSQECPREK-LURJTMIESA-N

Product Name

Cidofovir

Synthetic route

Cidofovir Analytical Methods

Cidofovir Specification

Related Products

Hot Products