6-chloropurine

Names

[ CAS No. ]:
87-42-3

[ Name ]:
6-chloropurine

[Synonym ]:
7H-Purine, 6-chloro-
5-chloropurine
1H-purine, 6-chloro-
1H-6-chloropurine
Purine,6-chloro
MFCD00075825
1H-Purine,6-chloro
6-Chloropurine
6-Chloro-1H-purine
chloropurine,6
EINECS 201-745-6
6-Chlorpurine
6-CP
6-CHLORO-9H-PURINE

Biological Activity

[Description]:

6-Chloropurine is a building block in chemical synthesis. Intermediate in the preparation of 9-alkylpurines and 6-rnercaptopurine. Antitumor activities[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Cancer

[In Vivo]

6-Chloropurine to S-(6-punnyl)glutathione and further metabolism of S-(6-punnyl)glutathione to 6-mercaptopunne may be involved in the mechanism of the 6-Chloropurine-induced antitumor activity[1]. 6-chloropurine and azaserine have been shown to have synergic antitumor properties in a variety of mouse neoplasms when administered simultaneously[1].

[References]

[1]. Hwang IY, et al. Detection and mechanisms of formation of S-(6-purinyl)glutathione and 6-mercaptopurine in rats given 6-chloropurine. J Pharmacol Exp Ther. 1993 Jan;264(1):41-6.

[2]. Sartorelli AC, et al. Comparative studies on the in vivo action of 6-chloropurine, 6-chloropurine ribonucleoside, and 6-chloro-9-ethylpurine on sarcoma 180 ascites cells. J Pharmacol Exp Ther. 1961 Oct;134:123-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
449.6±25.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C (dec.)(lit.)

[ Molecular Formula ]:
C₅H₃ClN₄

[ Molecular Weight ]:
154.557

[ Flash Point ]:
258.2±8.8 °C

[ Exact Mass ]:
154.004623

[ PSA ]:
54.46000

[ LogP ]:
0.13

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.740

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
5 g/L

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UO7520000

CHEMICAL NAME :: Purine, 6-chloro-

CAS REGISTRY NUMBER :: 87-42-3

LAST UPDATED :: 199410

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C5-H3-Cl-N4

MOLECULAR WEIGHT :: 154.57

WISWESSER LINE NOTATION :: T56 BM DN FN HNJ IG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 720 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 132 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 514 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD10 - Lethal Dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 230 mg/kg

TOXIC EFFECTS :: Blood - changes in bone marrow (not otherwise specified)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >316 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 mg/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

MUTATION DATA

TYPE OF TEST :: Host-mediated assay

TEST SYSTEM :: Rodent - mouse Bacteria - Salmonella typhimurium

DOSE/DURATION :: 25 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 26,455,1974 *** REVIEWS *** TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26-S36-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UO7520000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition

Bioorg. Med. Chem. Lett. 19 , 6433-6, (2009)

The synthesized compounds act as lipid peroxidation inhibitors and potent thrombin inhibitors.

The synthesis of novel fluorescent purine analogues modified by azacrown ether at C6

Bioorg. Med. Chem. Lett. 20(10) , 3098-102, (2010)

The synthesis and fluorescence properties of novel purine analogues linked azacrown ether at C6 position were investigated. These new purine analogues could be prepared from a series of 6-chloropurine...

Evidence for Watson-Crick and not Hoogsteen or wobble base pairing in the selection of nucleotides for insertion opposite pyrimidines and a thymine dimer by yeast DNA pol eta.

Biochemistry 44(12) , 4850-60, (2005)

We have recently reported that pyrene nucleotide is preferentially inserted opposite an abasic site, the 3'-T of a thymine dimer, and most undamaged bases by yeast DNA polymerase eta (pol eta). Becaus...