4897-25-0 Usage
Description
5-Chloro-1-methyl-4-nitroimidazole is an imidazole derivative, characterized as a white solid. It is an intermediate in the synthesis of azathioprine and is also present in the end product. 5-Chloro-1-methyl-4-nitroimidazole has been known to induce contact dermatitis in individuals working on azathioprine synthesis, and there is a possibility of cross-reactivity with other imidazoles such as tioconazole and econazole.
Uses
1. Used in Pharmaceutical Research:
5-Chloro-1-methyl-4-nitroimidazole is used as an intermediate in the synthesis of azathioprine, a medication used for the prevention of organ rejection in transplant patients and for the treatment of autoimmune diseases.
2. Used in Radiosensitization Studies:
5-Chloro-1-methyl-4-nitroimidazole is used as a radiosensitizer in rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells. This application aids in understanding the effects of radiation on cell biology and can potentially contribute to the development of new cancer treatment strategies.
3. Used in Synthesis of 5-aryl-1-methyl-4-nitroimidazoles:
5-Chloro-1-methyl-4-nitroimidazole is used as a starting material in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles through Suzuki coupling with arylboronic acids. This process is catalyzed by dichlorobis-(triphenylphosphine)palladium(II), K2CO3, and tetrabutylammonium bromide, which can lead to the development of new compounds with potential applications in various industries, including pharmaceuticals and materials science.
4. Used in Chemical Research and Development:
As an imidazole derivative, 5-Chloro-1-methyl-4-nitroimidazole can be utilized in the development of new chemical compounds and materials, potentially leading to advancements in various fields such as pharmaceuticals, agriculture, and materials science.
5. Used in Industrial Applications:
While not explicitly mentioned in the provided materials, imidazole derivatives like 5-Chloro-1-methyl-4-nitroimidazole may also find applications in industrial processes, such as in the synthesis of dyes, pigments, or other specialty chemicals. Further research and development in this area could lead to new uses and applications for this compound.
References
http://www.sigmaaldrich.com/catalog/product/aldrich/367532?lang=en®ion=US
Watts, M. E., et al. "Rapid-mix studies on the anomalous radiosensitization of mammalian cells by 5-chloro-1-methyl-4-nitromidazole." Int J Radiat Biol Relat Stud Phys Chem Med 38.6(1980):673-675.
Saadeh, H. A, I. M. Mosleh, and M. M. Elabadelah. "New synthesis and antiparasitic activity of model 5-aryl-1-methyl-4-nitroimidazoles. "Molecules 14.8(2009):2758-67.
Contact allergens
This intermediate in azathioprine synthesis is also present
in the end product. It induced contact dermatitis in
a man working on azathioprine synthesis. Cross-reactivity
is possible with imidazoles tioconazole and
econazole.
Check Digit Verification of cas no
The CAS Registry Mumber 4897-25-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,8,9 and 7 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4897-25:
(6*4)+(5*8)+(4*9)+(3*7)+(2*2)+(1*5)=130
130 % 10 = 0
So 4897-25-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H4ClN3O2/c1-7-2-6-4(3(7)5)8(9)10/h2H,1H3
4897-25-0Relevant articles and documents
Rational design of novel immunosuppressive drugs: Analogues of azathioprine lacking the 6-mercaptopurine substituent retain or have enhanced immunosuppressive effects
Crawford, Duncan J. K.,Maddocks, John L.,Jones, D. Neville,Szawlowski, Paul
, p. 2690 - 2695 (1996)
Clinical use of the immunosuppressive drug azathioprine is limited by potentially serious toxic effects related to depression of bone marrow function. The immunosuppressive and toxic properties of azathioprine are regarded as being properties of the cytotoxicity of its metabolite, 6- mercaptopurine (6-MP). However, azathioprine has an immunosuppressive effect additional to that attributable to 6-MP alone, and we propose that this is associated with an action of the methylnitroimidazolyl substituent. This suggests a route to the rational design of nontoxic immunosuppressants by replacing the 6-MP component of azathioprine with nontoxic thiols. We have synthesized and tested in vitro 24 such analogues, with two being further tested in vivo. In the human mixed lymphocyte reaction, virtually all compounds showed some degree of activity, 10 compounds being more active than azathioprine. In vivo, two compounds were more effective than azathioprine at prolonging graft survival in mice. In an oral toxicity study in male CD1 mice at doses equivalent to those at which azathioprine caused severe bone marrow depression both analogues had no toxic effects. Our results show that the immunosuppressive effects and bone marrow toxicity of azathioprine are not a consequence of release of 6-MP alone, and with appropriate modification can be separated, an approach which may lead to less toxic immunosuppressive drugs.
HETEROCYCLO-SUBSTITUTED IMIDAZOPYRAZINE PROTEIN TYROSINE KINASE INHIBITORS
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Page/Page column 39-40, (2009/06/27)
Novel heterocyclo-substituted imidazopyrazines and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic disorders.
Hetaryl imidazoles: A novel dual inhibitors of VEGF receptors I and II
Kiselyov, Alexander S.,Semenova, Marina,Semenov, Victor V.
, p. 1440 - 1444 (2007/10/03)
A novel potent derivatives of hetaryl imidazoles were described as inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). Several compounds display VEGFR-2 inhibitory activity reaching IC50 100 nM in both enzymatic and cellular assays. The compounds also inhibit the related tyrosine kinase, VEGFR-1. By controlling the substitution pattern on the 5-carboxamido functionality, both dual and specific VEGFR-2 thiazoles were identified.
