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34408-14-5

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34408-14-5 Usage

General Description

8-Chloroadenosine is a synthetic derivative of adenosine that has been studied for its potential as an anticancer agent. It is a nucleoside analog that has been shown to inhibit the growth of cancer cells by interfering with their DNA and RNA synthesis. 8-Chloroadenosine has also been found to induce apoptosis, or programmed cell death, in cancer cells, making it a promising candidate for chemotherapy treatment. Additionally, it has been investigated for its potential to enhance the effectiveness of other chemotherapy drugs when used in combination. Overall, 8-Chloroadenosine shows promise as a novel therapeutic agent for the treatment of various types of cancer.

Check Digit Verification of cas no

The CAS Registry Mumber 34408-14-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,4,0 and 8 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 34408-14:
(7*3)+(6*4)+(5*4)+(4*0)+(3*8)+(2*1)+(1*4)=95
95 % 10 = 5
So 34408-14-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)

34408-14-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

1.2 Other means of identification

Product number -
Other names 2-chloroadenosine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:34408-14-5 SDS

34408-14-5Synthetic route

adenosine
58-61-7

adenosine

8-chloroadenosine
34408-14-5

8-chloroadenosine

Conditions
ConditionsYield
With N-chloro-succinimide; acetic acid In N,N-dimethyl-formamide at 20℃; for 48h; Concentration; Reagent/catalyst;52%
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide for 3.5h; Ambient temperature;50%
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide at 0 - 25℃; for 2.5h;39%
8-mercaptoadenosine
3001-45-4

8-mercaptoadenosine

8-chloroadenosine
34408-14-5

8-chloroadenosine

Conditions
ConditionsYield
With N-chloro-succinimide In methanol at 20℃; for 3h;52%
N6-Benzyladenosine
4294-16-0

N6-Benzyladenosine

A

8-chloroadenosine
34408-14-5

8-chloroadenosine

B

6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine
1427459-38-8

6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine

Conditions
ConditionsYield
With N-chloro-succinimide In N,N-dimethyl-formamide at 45℃; for 18h;A n/a
B 20%
N-chloro-succinamide

N-chloro-succinamide

water
7732-18-5

water

adenosine
58-61-7

adenosine

8-chloroadenosine
34408-14-5

8-chloroadenosine

Conditions
ConditionsYield
With acetic acid In methanol; N,N-dimethyl-formamide0.8 g (65%)
8-bromoadenosine
2946-39-6

8-bromoadenosine

8-chloroadenosine
34408-14-5

8-chloroadenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thiourea / ethanol / 1 h / Reflux
2: N-chloro-succinimide / methanol / 3 h / 20 °C
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

methylamine
74-89-5

methylamine

8-Methylaminoadenosine
13389-13-4

8-Methylaminoadenosine

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 18.5h;93%
With triethylamine at 20℃; for 20h;93%
8-chloroadenosine
34408-14-5

8-chloroadenosine

acetic anhydride
108-24-7

acetic anhydride

8-chloro-2',3',5'-tri-O-acetyladenosine
64344-20-3

8-chloro-2',3',5'-tri-O-acetyladenosine

Conditions
ConditionsYield
With pyridine for 16h; Ambient temperature;88%
8-chloroadenosine
34408-14-5

8-chloroadenosine

acetone
67-64-1

acetone

2’,3’-O-isopropylidene-8-chloroadenosine

2’,3’-O-isopropylidene-8-chloroadenosine

Conditions
ConditionsYield
With perchloric acid at 20℃; for 0.5h;79%
8-chloroadenosine
34408-14-5

8-chloroadenosine

Phenoxyacetyl chloride
701-99-5

Phenoxyacetyl chloride

N6-phenoxyacetyl-8-chloroadenosine
508179-29-1

N6-phenoxyacetyl-8-chloroadenosine

Conditions
ConditionsYield
With pyridine; 1,2,4-Triazole; chloro-trimethyl-silane In acetonitrile at 25 - 55℃; for 8h;71%
phenyl-1-yl-L-glycine benzyl ester phosphorochloridate
926308-62-5

phenyl-1-yl-L-glycine benzyl ester phosphorochloridate

8-chloroadenosine
34408-14-5

8-chloroadenosine

benzyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)acetate

benzyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)acetate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;28%
8-chloroadenosine
34408-14-5

8-chloroadenosine

benzyl 2-aminoacetate hydrochloride
2462-31-9

benzyl 2-aminoacetate hydrochloride

8-chloroadenosine 5’-O-bis(benzyloxyglycin-N-yl)phosphate

8-chloroadenosine 5’-O-bis(benzyloxyglycin-N-yl)phosphate

Conditions
ConditionsYield
Stage #1: 8-chloroadenosine With phosphorous acid trimethyl ester; trichlorophosphate at -5 - 20℃; for 4h;
Stage #2: benzyl 2-aminoacetate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 20h;
27%
8-chloroadenosine
34408-14-5

8-chloroadenosine

naphth-1-yl-glycine pent-1-yl ester phosphorochloridate

naphth-1-yl-glycine pent-1-yl ester phosphorochloridate

5’-([(pent-1-yloxy-glycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

5’-([(pent-1-yloxy-glycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;15%
8-chloroadenosine
34408-14-5

8-chloroadenosine

phenyl-1-yl-L-glycine cyclohexyl ester phosphorochloridate

phenyl-1-yl-L-glycine cyclohexyl ester phosphorochloridate

cyclohexyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)acetate

cyclohexyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)acetate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;14%
phenyl (benzyloxy-D-alaninyl)phosphorochloridate

phenyl (benzyloxy-D-alaninyl)phosphorochloridate

8-chloroadenosine
34408-14-5

8-chloroadenosine

5’-([(benzyloxy-D-alanin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

5’-([(benzyloxy-D-alanin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

Conditions
ConditionsYield
Stage #1: 8-chloroadenosine With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: phenyl (benzyloxy-D-alaninyl)phosphorochloridate In tetrahydrofuran
11%
8-chloroadenosine
34408-14-5

8-chloroadenosine

naphth-1-yl-glycine benzyl ester phosphorochloridate
1228377-60-3

naphth-1-yl-glycine benzyl ester phosphorochloridate

5’-([(benzyloxyglycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

5’-([(benzyloxyglycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;4%
8-chloroadenosine
34408-14-5

8-chloroadenosine

naphth-1-yl-glycine ethyl ester phosphorochloridate

naphth-1-yl-glycine ethyl ester phosphorochloridate

5’-([(ethyloxy-glycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

5’-([(ethyloxy-glycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;4%
8-chloroadenosine
34408-14-5

8-chloroadenosine

phenyl(benzyloxy-L-alaninyl)phosphorochloridate
183370-70-9

phenyl(benzyloxy-L-alaninyl)phosphorochloridate

(2S)-benzyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

(2S)-benzyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;2%
8-chloroadenosine
34408-14-5

8-chloroadenosine

O-phenyl-N-(S)-1-(cyclohexoxycarbonyl)ethylphosphoramidic chloride
220592-67-6

O-phenyl-N-(S)-1-(cyclohexoxycarbonyl)ethylphosphoramidic chloride

5’-([(cyclohexyloxy-L-alanin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

5’-([(cyclohexyloxy-L-alanin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

Conditions
ConditionsYield
Stage #1: 8-chloroadenosine With pyridine; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: O-phenyl-N-(S)-1-(cyclohexoxycarbonyl)ethylphosphoramidic chloride In tetrahydrofuran for 24h;
2%
8-chloroadenosine
34408-14-5

8-chloroadenosine

C15H23ClNO4P

C15H23ClNO4P

5’-([(neopentyloxy-2,2-dimethylglycin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

5’-([(neopentyloxy-2,2-dimethylglycin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

Conditions
ConditionsYield
Stage #1: 8-chloroadenosine With pyridine; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: C15H23ClNO4P In tetrahydrofuran for 24h;
2%
methyl bromide
74-83-9

methyl bromide

8-chloroadenosine
34408-14-5

8-chloroadenosine

6-Amino-8-chloro-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methyl-9H-purin-1-ium; bromide

6-Amino-8-chloro-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methyl-9H-purin-1-ium; bromide

Conditions
ConditionsYield
In N,N-dimethyl acetamide for 120h; Ambient temperature;
8-chloroadenosine
34408-14-5

8-chloroadenosine

A

8chloroadenosine-5'-phosphate

8chloroadenosine-5'-phosphate

B

8-chloroadenosine-5'-diphosphate

8-chloroadenosine-5'-diphosphate

C

8-chloroadenosine-5'-triphosphate

8-chloroadenosine-5'-triphosphate

Conditions
ConditionsYield
With Tetraethyl pyrophosphate; phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate Yield given. Multistep reaction. Yields of byproduct given;
8-chloroadenosine
34408-14-5

8-chloroadenosine

N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-8-chloro-9H-purin-6-yl)-2-phenoxy-acetamide
508179-30-4

N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-8-chloro-9H-purin-6-yl)-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C
2: 58 percent / DMAP / pyridine / 19 h
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

N-{9-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-yl}-2-phenoxy-acetamide
508179-32-6

N-{9-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-yl}-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C
2: 58 percent / DMAP / pyridine / 19 h
3: 38 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

N-{9-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-yl}-2-phenoxy-acetamide
508179-31-5

N-{9-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-yl}-2-phenoxy-acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C
2: 58 percent / DMAP / pyridine / 19 h
3: 16 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

Succinic acid mono-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-[8-chloro-6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl} ester

Succinic acid mono-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-[8-chloro-6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl} ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C
2: 58 percent / DMAP / pyridine / 19 h
3: 38 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C
4: 71 percent / DMAP / pyridine / 12 h / 25 °C
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[8-chloro-6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[8-chloro-6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C
2: 58 percent / DMAP / pyridine / 19 h
3: 16 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C
4: 50 percent / 2,4,6-collidine; N-methylimidazole / tetrahydrofuran / 4 h / 25 °C
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

8-Chloro-purine riboside

8-Chloro-purine riboside

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / pyridine / 16 h / Ambient temperature
2: 39 percent / t-butyl nitrite / tetrahydrofuran / 1 h / Heating
3: 37 percent / aq. NH4HCO3 / 120 h / Ambient temperature; porcine liver esterase
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

8-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
157025-49-5

8-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / pyridine / 16 h / Ambient temperature
2: 39 percent / t-butyl nitrite / tetrahydrofuran / 1 h / Heating
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

8-chloro-1-methyladenine
92001-48-4

8-chloro-1-methyladenine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-acetamide / 120 h / Ambient temperature
2: glacial acetic acid / 2.5 h / Heating
3: 232 mg / conc. aq. ammonia
View Scheme
8-chloroadenosine
34408-14-5

8-chloroadenosine

6-Amino-8-chloro-1-methyl-9H-purin-1-ium; bromide

6-Amino-8-chloro-1-methyl-9H-purin-1-ium; bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-acetamide / 120 h / Ambient temperature
2: glacial acetic acid / 2.5 h / Heating
View Scheme

34408-14-5Relevant articles and documents

Brentnall,Hutchinson

, p. 2595 (1972)

ADENOSINE DERIVATIVES FOR USE IN THE TREATMENT OF CANCER

-

Page/Page column 55; 56, (2018/01/17)

The present invention relates to chemical compounds of formula (I) as defined in the amended claims, their preparation and their use in the treatment of cancer.

6,8-DISUBSTITUTED PURINE COMPOSITIONS

-

Paragraph 0127, (2013/03/28)

6,8-Disubstituted purines which can be used in drug and cosmetic compositions and/or applications are provided. These 6,8-disubstituted purines have a wide range of biological activities, including for example anti-inflammatory, anti-senescent, as well as well as other activities which are especially useful in pharmaceutical and cosmetic applications. The 6,8-disubstituted purine compounds and compositions containing such 6,8-disubstituted purines provide growth-regulatory, differentiating, antisenescent and antiaging properties with improved selectivities and efficiencies and lower toxicities than analogues known heretofore.

8-Chloroadenosine 3', 5'-cyclic monophosphate preparations

-

, (2008/06/13)

The compound 8-Chloroadenosine 3',5'-cyclic phosphate is used to treat malignant tumors in warm blooded animals. Two novel single step syntheses of 8-chloroadenosine 3',5'-cyclic phosphate and other related adenine and adenosine compounds from corresponding adenosine 3', 5'-cyclic phosphate and other respective related adenosine compounds are disclosed.

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