448287-48-7Relevant academic research and scientific papers
Microwave-assisted suzuki cross-coupling reaction, a key step in the synthesis of polycyclic aromatic hydrocarbons and their metabolites
Sharma, Arun K.,Gowdahalli, Krishnegowda,Krzeminski, Jacek,Amin, Shantu
, p. 8987 - 8989 (2008/03/12)
(Chemical Equation Presented) A highly efficient and general method for Suzuki cross-coupling reaction en route to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and their metabolites has been developed. Microwave irradiation of aryl bromides 1
Synthesis, in vitro metabolism, cell transformation, mutagenicity, and DNA adduction of dibenzo[c,mno] chrysene
Desai, Dhimant,Sharma, Arun K.,Lin, Jyh-Ming,Krzeminski, Jacek,Pimentel, Maria,El-Bayoumy, Karam,Nesnow, Stephen,Amin, Shantu
, p. 964 - 971 (2008/04/18)
Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants. Due to its structural similarity with the potent carcinogen dibenzo [a,l] pyrene (DB [a,l]P) and because of its environmental presence, dibenzo[c,mno]chrysene (naphtho[1,2-a]pyrene, N[1,2-a]P) is of considerable research interest. We therefore developed an efficient synthesis of N[1,2-a]P, and examined its in vitro metabolism by male Sprague Dawley rat liver S9 fraction. Its mutagenic activity in S. typhimurium TA 100 and its morphological cell transforming ability in mouse embryo fibroblasts were evaluated. On the basis of spectral analyses, the in vitro major metabolites were identified as the fjord region dihydrodiol trans-9,10-dihydroxy-9,10- dihydro-N[1,2-a]P (N[1,2-a]P-9,10-dihydrodiol), the K-region diols N[1,2-a]P-4,5-dihydrodiol and N[1,2-a]P-7,8-dihydrodiol, and also the 1-, 3-, and 10-hydroxy-N[1,2-a]P; the structure of N[1,2-a]P-9,10-dihydrodiol was also confirmed by independent synthesis. In assays with S. typhimurium TA 100, N[1,2-a]P-9,10-dihydrodiol was half as mutagenic as (±)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene (B[a]P-7,8-dihydrodiol) at ≥ nmol/plate. N[1,2-a]P-9,- 10-dihydrodiol was much more mutagenic than N[1,2-a]P at all dose levels, suggesting that the N[1,2-a]P-9,10-dihydrodiol is the likely proximate mutagen of N[1,2-a]P. Evaluation of morphological cell transformation in C3H10T1/2C18 mouse embryo fibroblasts revealed that N[1,2-a]P was comparable to B[a]P. We further examined the pattern of in vitro adduct formation between calf thymus DNA and (±)-anti-9,10-dihydroxy-9,10-dihydro-11,12-epoxy- 9,10,11,12-tetrahydro-N[1,2-a]P (N[1,2-a]PDE) and found that dG-adduct formation is 2.9-fold greater than dA-adduct formation. On the basis of our results and those reported in the literature, our working hypothesis is that N[1,2-a]P may be added to the list of potent carcinogens that includes DB [a,l]P. This hypothesis is currently being tested in our laboratory.
A convenient and general synthesis of cata- and peri-condensed polycyclic aromatic hydrocarbons with a Fjord-region
Kumar, Subodh
, p. 841 - 844 (2007/10/03)
Cata- and peri-condensed polycyclic aromatic hydrocarbons (PAHs) 10a-d and 11 have been conveniently synthesized by the application of Suzuki cross-coupling reaction. In three to four steps, these PAHs having fjord-region were obtained in an overall yield of 35-51% from commercially or easily accessible aryl boronic acids and aryl bromides.
