36746-27-7

Upstream product

• 216171-27-6 5-formyl-1'-methanesulfonyl-2,2'-dipyrrylmethane 
• 21211-65-4 di(pyrrol-2-yl)methane 
• 1864-94-4 phenyl formate 
• 683-18-1 dibutyltin chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 1003-29-8 2-pyrrole aldehyde 
• 123892-38-6 1-(methylsulfonyl)-1H-pyrrole-2-carbaldehyde 
• 202580-86-7 (1-methanesulfonyl-1H-pyrrol-2-yl)methanol 
• 216171-18-5 2-chloromethyl-1-methanesulfonyl-1H-pyrrole 
• 216171-26-5 5-(1,3-dithiolan-2-yl)-1'-methanesulfonyl-2,2'-dipyrrylmethane 
• 216171-28-7 C₁₆H₂₂N₂O₄S 
• 3724-43-4 Vilsmeier reagent 

Downstream Products

• 13007-95-9 tetraphenylporphinatoMg 
• 101-60-0 porphyrin 
• 40882-83-5 5,10,15,20-tetra(3-pyridyl)porphyrin 
• 16834-13-2 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphine 
• 4396-11-6 calix[4]pyrrole 

Relevant academic research and scientific papers

Synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives via reductive heteroarylation

An efficient and general reductive heteroarylation approach toward the synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives has been developed. Thus, treatment of acylpyrrole or acylindole derivatives with indoles or pyrroles in the presence of a combination of sodium borohydride and acetic acid resulted in the formation of the title compounds in moderate to excellent isolated yields.

The effect of pyridyl substituents on the thermodynamics of porphyrin binding to G-quadruplex DNA

Most of the G-quadruplex interactive molecules reported to date contain extended aromatic flat ring systems and are believed to bind principally by π-π stacking on the end G-tetrads of the quadruplex structure. One such molecule, TMPyP4, (5,10,15,20-tetra(N-methyl-4-pyridyl)porphyrin), exhibits high affinity and some selectivity for G-quadruplex DNA over duplex DNA. Although not a realistic drug candidate, TMPyP4 is used in many nucleic acid research laboratories as a model ligand for the study of small molecule G-quadruplex interactions. Here we report on the synthesis and G-quadruplex interactions of four new cationic porphyrin ligands having only 1, 2, or 3 (N-methyl-4-pyridyl) substituents. The four new ligands are: P(5) (5-(N-methyl-4-pyridyl)porphyrin), P(5,10) (5,10-di(N-methyl-4-pyridyl)porphyrin), P(5,15) (5,15-di(N-methyl-4- pyridyl)porphyrin), and P(5,10,15) (5,10,15-tri(N-methyl-4-pyridyl)porphyrin). Even though these compounds have been previously synthesized, we report alternative synthetic routes that are more efficient and that result in higher yields. We have used ITC, CD, and ESI-MS to explore the effects of the number of N-methyl-4-pyridyl substituents and the substituent position on the porphyrin on the G-quadruplex binding energetics. The relative affinities for binding these ligands to the WT Bcl-2 promoter sequence G-quadruplex are: K TMPyP4 ≈ KP(5,15) > KP(5,10,15) >>> KP(5,10), KP(5). The saturation stoichiometry is 2:1 for both P(5,15) and P(5,10,15), while neither P(5) nor P(5,10) exhibit significant complex formation with the WT Bcl-2 promoter sequence G-quadruplex. Additionally, binding of P(5,15) appears to interact by an 'intercalation mode' while P(5,10,15) appears to interact by an 'end-stacking mode'.

METHOD OF MAKING PORPHYRINS

A method of making a compound of Formula I: is carried out by condensing a pair of compounds of Formula II (which pair may be the same or different), or by condensing a compound of Formula III with a compound Formula IV, to produce a compound of Formula I. The condensing step may be carried out with a metal salt under basic conditions.

Direct synthesis of magnesium porphine via 1-formyldipyrromethane

(Chemical Equation Presented) The reaction of 1-formyldipyrromethane (100 mM) in toluene at 115°C containing DBU (10 mol equiv) and MgBr2 (3 mol equiv) in the presence of air affords the magnesium chelate Mg(II) porphine in 30-40% yield. The advantages of the new method include simplicity, high concentration, chromatography-free purification, gram-scale synthesis, and avoidance of the poorly soluble free base porphine. Mg(II) porphine exhibits good solubility in common organic solvents and is a valuable core scaffold for derivatization.

Synthesis of 1-formyldipyrromethanes

1-Formyldipyrromethanes are versatile precursors to porphyrins and chlorins. Two methods of synthesis of 1-formyldipyrromethanes have been investigated: (1) Vilsmeier formylation followed by selective removal of the unwanted 1,9-diformyldipyrromethane by

The reaction of N-magnesium derivatives of pyrroles with N- mesylchloromethylpyrroles: A synthesis of dipyrrylmethanes

Attachment of an alkyl- or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N-tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N-mesylated chloromethylpyrroles are handleable materials which react smoothly with N- magnesium derivatives of pyrroles to provide a novel route for synthesis of dipyrrylmethanes. Several examples of this synthesis are described, including the construction of molecules carrying deuterium at the interpyrrolic methylene group.