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1-beta-D-Arabinofuranosylcytosine hydrochloride

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Name

1-beta-D-Arabinofuranosylcytosine hydrochloride

EINECS 200-713-9
CAS No. 69-74-9 Density N/A
PSA 130.83000 LogP -1.17980
Solubility soluble in water Melting Point 197-198 °C(lit.)
Formula C9H13N3O5.HCl Boiling Point 545.7 °C at 760 mmHg
Molecular Weight 279.68 Flash Point 283.8 °C
Transport Information N/A Appearance fluffy white powder
Safety 26-36/37 Risk Codes 36-43-63
Molecular Structure Molecular Structure of 69-74-9 (1-beta-D-Arabinofuranosylcytosine hydrochloride) Hazard Symbols HarmfulXn
Synonyms

2(1H)-Pyrimidinone,4-amino-1-b-D-arabinofuranosyl-,monohydrochloride (9CI);Cytosine, 1-b-D-arabinofuranosyl-, monohydrochloride (8CI);1-b-D-Arabinofuranosylcytosinehydrochloride;1-b-D-Arabinofuranosylcytosinemonohydrochloride;Arabinofuranosylcytosine hydrochloride;Arabinosylcytosinehydrochloride;Aracytidine hydrochloride;Cytosinearabinoside hydrochloride;Spongocytidine-hydrochloride;U 19920A;Cytarabine HCl;

Article Data 5

1-beta-D-Arabinofuranosylcytosine hydrochloride Synthetic route

147-94-4

arabinosyl cytosine

69-74-9

cytarabine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 2 - 25℃; for 4h;96%
With hydrogenchloride In diethyl ether
10212-25-6

ancitabine hydrochloride

69-74-9

cytarabine hydrochloride

Conditions
ConditionsYield
With ammonia In water at 80℃; for 0.5h; Temperature;62.4%
69-74-9

cytarabine hydrochloride

219797-98-5

3-Acryloylamino-propionic acid pentafluorophenyl ester

186594-89-8

N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In pyridine at 80℃;95%
69-74-9

cytarabine hydrochloride

17676-65-2

4-amino-5-chloro-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2(1H)-one

Conditions
ConditionsYield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide for 1h; Ambient temperature;83.9%
69-74-9

cytarabine hydrochloride

219797-99-6

4-Acryloylamino-butyric acid pentafluorophenyl ester

186594-93-4

N-(3-(N4-carbamoyl-1-(β-D-arabinofuranosyl)cytosine)-propyl)acrylamide

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In pyridine at 80℃;78%
69-74-9

cytarabine hydrochloride

elacytarabine

Conditions
ConditionsYield
In ISOPROPYLAMIDE at 30℃; for 22h;72%
69-74-9

cytarabine hydrochloride

gondoic acid chloride

CP-4057

Conditions
ConditionsYield
In ISOPROPYLAMIDE; N,N-dimethyl-formamide at 25℃; for 24h;66%
1257411-82-7

N-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-yl)-6-oxo-6-(2-thioxothiazolidin-3-yl)hexanamide

69-74-9

cytarabine hydrochloride

1257411-83-8

N1-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-yl)-N6-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)adipamide

Conditions
ConditionsYield
With pyridine at 50℃;66%
69-74-9

cytarabine hydrochloride

82626-74-2

2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid

1257411-86-1

2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Conditions
ConditionsYield
Stage #1: 2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: cytarabine hydrochloride In N,N-dimethyl-formamide Inert atmosphere;
65%

2-(pyridin-2-yldisulfaneyl)ethyl 1H-1,2,4-triazole-1-carboxylate

69-74-9

cytarabine hydrochloride

2-(pyridin-2-yldisulfaneyl)ethyl (1-((3S,4S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;63%

1-beta-D-Arabinofuranosylcytosine hydrochloride Specification

The IUPAC name of 1-beta-D-Arabinofuranosylcytosine hydrochloride is 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one hydrochloride. With the CAS registry number 69-74-9, it is also named as Cytarabine hydrochloride. The product's categories are Pyridines, Pyrimidines, Purines and Pteredines. Besides, it is fluffy white powder, which should be stored at 2-8 °C. It undergoes decomposition in acidic solutions. In addition, its molecular formula is C9H13N3O5.HCl and molecular weight is 279.68.

The other characteristics of this product can be summarized as: (1)EINECS: 200-713-9; (2)ACD/LogP: -1.94; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -1.94; (5)ACD/LogD (pH 7.4): -1.94; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 2.1; (9)ACD/KOC (pH 7.4): 2.11; (10)#H bond acceptors: 8; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 5; (13)Polar Surface Area: 72.83 Å2; (14)Melting Point: 180-182 °C; (15)Flash Point: 283.8 °C; (16)Enthalpy of Vaporization: 94.8 kJ/mol; (17)Boiling Point: 545.7 °C at 760 mmHg; (18)Vapour Pressure: 3.5E-14 mmHg at 25 °C.

Preparation and Uses of 1-beta-D-Arabinofuranosylcytosine hydrochloride: this chemical can be prepared by 5'-CMP or Calcium Gluconate. Additionally, it is ntineoplastic agent that inhibits the synthesis of DNA. It is mainly used for the treatment of acute leukemia and gastrointestinal cancer. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties.

When you are using this chemical, please be cautious about it as the following: it irritates to eyes, and may cause sensitization by skin contact. It is also possible risk of harm to the unborn child. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure.
(1)SMILES: Cl.O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@@H]2O)CO
(2)InChI: InChI=1/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1
(3)InChIKey: KCURWTAZOZXKSJ-JBMRGDGGBO

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 172mg/kg (172mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 353, 1974.
monkey LD50 intravenous 396mg/kg (396mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: NAUSEA OR VOMITING
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 353, 1974.
mouse LD50 intraperitoneal 825mg/kg (825mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1255, 1972.
mouse LD50 oral 826mg/kg (826mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 2262mg/kg (2262mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 intraperitoneal 5500mg/kg (5500mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1255, 1972.
rat LD50 oral > 3200mg/kg (3200mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1255, 1972.

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