6161-23-5 Usage
Description
3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE, with the CAS number 6161-23-5, is a synthetic compound that plays a significant role in organic synthesis. It is a derivative of 2'-deoxyuridine, a naturally occurring nucleoside, where the 3' and 5' hydroxyl groups are acetylated, and a bromine atom is introduced at the 5-position. This modification enhances its reactivity and stability, making it a valuable intermediate in the synthesis of various biologically active molecules.
Uses
Used in Organic Synthesis:
3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE is used as a key intermediate in the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure allows for further chemical modifications, enabling the development of new drugs with improved properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE serves as a versatile building block for the design and synthesis of novel nucleoside analogs. These analogs have the potential to target specific enzymes or receptors involved in various diseases, including viral infections, cancer, and genetic disorders.
Used in Antiviral Drug Development:
3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE is used as a starting material for the development of antiviral agents. Its unique structure can be exploited to create nucleoside analogs that inhibit viral replication, providing a new avenue for the treatment of viral diseases such as hepatitis, herpes, and human immunodeficiency virus (HIV) infections.
Used in Cancer Research:
In cancer research, 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE can be utilized to develop nucleoside analogs that target cancer cells specifically. These analogs can be designed to interfere with the replication and survival of cancer cells, leading to their death and potentially offering a new therapeutic approach for cancer treatment.
Used in Genetic Research:
3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE can also be employed in genetic research to study the mechanisms of DNA replication, repair, and transcription. Its unique structure allows for the investigation of how specific modifications to nucleosides can impact these processes, potentially leading to a better understanding of genetic diseases and the development of targeted therapies.
Check Digit Verification of cas no
The CAS Registry Mumber 6161-23-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,6 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 6161-23:
(6*6)+(5*1)+(4*6)+(3*1)+(2*2)+(1*3)=75
75 % 10 = 5
So 6161-23-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H15BrN2O7/c1-6(17)21-5-10-9(22-7(2)18)3-11(23-10)16-4-8(14)12(19)15-13(16)20/h4,9-11H,3,5H2,1-2H3,(H,15,19,20)/t9-,10-,11-/m1/s1
6161-23-5Relevant articles and documents
Why does the type of halogen atom matter for the radiosensitizing properties of 5-halogen substituted 4-thio-20-deoxyuridines?
Spisz, Paulina,Zdrowowicz, Magdalena,Makurat, Samanta,Kozak, Witold,Skotnicki, Konrad,Bobrowski, Krzysztof,Rak, Janusz
, (2019)
Radiosensitizing properties of substituted uridines are of great importance for radiotherapy. Very recently, we confirmed 5-iodo-4-thio-20-deoxyuridine (ISdU) as an efficient agent, increasing the extent of tumor cell killing with ionizing radiation. To our surprise, a similar derivative of 4-thio-2’-deoxyuridine, 5-bromo-4-thio-20-deoxyuridine (BrSdU), does not show radiosensitizing properties at all. In order to explain this remarkable difference, we carried out a radiolytic (stationary and pulse) and quantum chemical studies, which allowed the pathways to all radioproducts to be rationalized. In contrast to ISdU solutions, where radiolysis leads to 4-thio-2’-deoxyuridine and its dimer, no dissociative electron attachment (DEA) products were observed for BrSdU. This observation seems to explain the lack of radiosensitizing properties of BrSdU since the efficient formation of the uridine-5-yl radical, induced by electron attachment to the modified nucleoside, is suggested to be an indispensable attribute of radiosensitizing uridines. A larger activation barrier for DEA in BrSdU, as compared to ISdU, is probably responsible for the closure of DEA channel in the former system. Indeed, besides DEA, the XSdU anions may undergo competitive protonation, which makes the release of X? kinetically forbidden.
Functionalized tricyclic cytosine analogues provide nucleoside fluorophores with improved photophysical properties and a range of solvent sensitivities
Rodgers, Brittney J.,Elsharif, Nada A.,Vashisht, Nisha,Mingus, MacY M.,Mulvahill, Mark A.,Stengel, Gudrun,Kuchta, Robert D.,Purse, Byron W.
supporting information, p. 2010 - 2015 (2014/03/21)
Tricyclic cytosines (tC and tCO frameworks) have emerged as a unique class of fluorescent nucleobase analogues that minimally perturb the structure of B-form DNA and that are not quenched in duplex nucleic acids. Systematic derivatization of th
Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin
Rayala, Ramanjaneyulu,Wnuk, Stanislaw F.
experimental part, p. 3333 - 3336 (2012/07/30)
Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5-dimethylhydantoin in aprotic solvents such as CH 2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination.
