853-37-2

Upstream product

• 72867-44-8 (N-benzoyl-4-chloro-anilino)-phenyl-acetonitrile 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 106-47-8 4-chloro-aniline 
• 495-71-6 phenacylacetophenone 
• 25287-19-8 N-(4-chlorophenyl)-(1-phenylethylidene)amine 
• 54951-51-8 1,4-bis(4-chlorophenyl)-2,6-diphenyl-1,4-dihydropyrazine 
• 53181-22-9 2-[(4-chlorophenyl)amino]-1-phenylethanone 
• 70-11-1 α-bromoacetophenone 
• 1000775-45-0 N,N-bis(phenacyl)-4-chloroaniline 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Diaryl- and triaryl-pyrrole derivatives: Inhibitors of the MDM2-p53 and MDMX-p53 protein-protein interactions

Screening identified 2-(3-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)- ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b] thiophene-3-carbonitrile as an MDM2-p53 inhibitor (IC50 = 12.3 μM). MDM2-p53 and MDMX-p53 activity was seen for 5-((1-(4-chlorophenyl)-2,5- diphenyl-1H-pyrrol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (MDM2 IC50 = 0.11 μM; MDMX IC50 = 4.2 μM) and 5-((1-(4-nitrophenyl)-2,5-diphenyl-1H-pyrrol-3-yl)methylene)pyrimidine-2,4,6(1H, 3H,5H)-trione (MDM2 IC50 = 0.15 μM; MDMX IC50 = 4.2 μM), and cellular activity consistent with p53 activation in MDM2 amplified cells. Further SAR studies demonstrated the requirement for the triarylpyrrole moiety for MDMX-p53 activity but not for MDM2-p53 inhibition. The Royal Society of Chemistry.

Photochemistry of N-heterocycles. 7: Light induced reductive ring contractions of sixmembered cyclic iminium ions

Photochemically induced reductive ring contractions, previously observed for 2,5-dihydro-1,2,4-triazines, have also been verified for 1,4-dihydropyrimidines 2a,b, the dihydro-1,2,4,5-tetrazine 9, and dihydro-1,3,5-triazines 11a,b giving rise to fivemembered fully unsaturated heterocycles (pyrroles 4a,b, imidazoles 13a,b, and triazole 10, respectively). The 1,4-dihydropyrazines 15a-j tend to decompose in acidified 2-propanol in the dark, but on irradiation they also undergo reductive ring contraction furnishing solely the 1,2,5-triarylpyrroles 16a-d rather than the (a priori also possible) isomeric 1,3,4-triarylpyrroles 17a-d. In contrast, the 3,6-diphenylpyrid-azine 18 gives the 4-isopropyl-analogue 19 in low yield upon irradiation in hydrogen chloride saturated 2-propanol. Wiley-VCH Verlag GmbH, 2000.

Synthesis of Substituted Pyrroles by Intramolecular Condensation of a Wittig Reagent with the Carbonyl Group of a Tertiary Amide

1,2,5-Trisubstituted pyrroles are obtained in 50-100percent yields by addition of the conjugate bases of open-chain analogues of Reissert compounds to the vinyltriphenylphosphonium cation, with subsequent cyclization by an intramolecular Wittig reaction and base-catalyzed elimination of hydrogen cyanide.