214072-73-8

Upstream product

• 56979-57-8 2-benzyloxy-5-methoxybenzaldehyde 
• 67-56-1 methanol 
• 121124-94-5 2-benzyloxy-5-bromobenzaldehyde 
• 100-39-0 benzyl bromide 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 214072-74-9 2-benzyloxy-5-methoxybenzyl chloride 
• 118237-06-2 ethyl 2-(2-benzyloxy-5-methoxy)benzyl-3-oxobutanoate 
• 118252-37-2 2,4-diamino-5-methyl-6-(2-hydroxy-5-methoxybenzyl)pyrido [2,3-d ]pyrimidine 
• 118252-40-7 2,4-diamino-5-methyl-6-(2'-benzyloxy-5'-methoxybenzyl)-7-chloropyrid[2,3-d]pyrimidine 
• 118252-39-4 2,4-diamino-5-methyl-6-(2'-benzyloxy-5'-methoxybenzyl)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 860771-39-7 4-[2-(2,4-diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-ylmethyl)-4-methoxy-phenoxy]-butyric acid ethyl ester 
• 1313702-02-1 (4-methoxy-2-hydroxymethylphenyl)phenylmethanol 
• 1334484-12-6 N-(2-(benzyloxy)-5-methoxybenzyl)-2-fluoro-N-(2-phenoxyphenyl)acetamide 
• 1334484-13-7 2-fluoro-N-(2-hydroxy-5-methoxybenzyl)-N-(2-phenoxyphenyl)-acetamide 

Relevant academic research and scientific papers

Total synthesis of plagiochin G and derivatives as potential cancer chemopreventive agents

A new and efficient total synthesis has been developed to obtain plagiochin G (22), a macrocyclic bisbibenzyl, and four derivatives. The key 16-membered ring containing biphenyl ether and biaryl units was closed via an intramolecular SNAr reaction. All synthesized macrocyclic bisbibenzyls inhibited Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells and, thus, are potential cancer chemopreventive agents.

Functionalization at Will of Rim-Differentiated Pillar[5]arenes

The development of an efficient synthetic route toward rim-differentiated C5-symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffo

Unexpected observations during the total synthesis of calothrixin B-sodium methoxide as a source of hydride

During the total synthesis of calothrixin B, various novel and unexpected results were noticed such as cleavage of C-N bond in imine using sodium cyanoborohydride, sodium methoxide as a hydride source for reduction, deformylation in the presence of bromine, and deacylation using ceric ammonium nitrate (CAN). A detailed mechanism has been proposed for the unexpected results and a few of them are generalized. Temperature dependent NMR studies have been carried out for confirmation of the structure of one of the intermediates in the synthetic sequence.

Neighboring lithium-assisted [1,2]-wittig rearrangement: Practical access to diarylmethanol-based 1,4-diols and optically active binol derivatives with axial and sp3-central chirality

A facile and practical methodology for the synthesis of synthetically useful diarylmethanol-based 1,4-diols and enantiomerically pure BINOL-derived diols with axial and sp3-central chirality has been developed through neighboring lithium-promot

Synthesis of [11C]PBR06 and [18F]PBR06 as agents for positron emission tomographic (PET) imaging of the translocator protein (TSPO)

The translocator protein 18 kDa (TSPO) is an attractive target for molecular imaging of neuroinflammation and tumor progression. [ 18F]PBR06, a fluorine-18 labeled form of PBR06, is a promising PET TSPO radioligand originally developed at NIMH.

Design, synthesis, and antifolate activity of new analogues of piritrexim and other diaminopyrimidine dihydrofolate reductase inhibitors with ω-carboxyalkoxy or ω-carboxy-1-alkynyl substitution in the side chain

As part of a search for dihydrofolate reductase (DHFR) inhibitors combining the high potency of piritrexim (PTX) with the high antiparasitic vs mammalian selectivity of trimethoprim (TMP), the heretofore undescribed 2,4-diamino-6-(2′,5′-disubstituted benzyl)pyrido[2,3-d]pyrimidines 6-14 with O-(ω-carboxyalkyl) or ω-carboxy-1-alkynyl groups on the benzyl moiety were synthesized and tested against Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium DHFR vs rat DHFR. Three N-(2,4-diaminopteridin-6-yl)methyl)-2′-(ω-carboxy-1-alkynyl) -dibenz[b,f]azepines (19-21) were also synthesized and tested. The pyridopyrimidine with the best combination of potency and selectivity was 2,4-diamino-5-methyl-6-[2′-(5-carboxy-1-butynyl)-5′-methoxy]benzyl] pyrimidine (13), with an IC50 value of 0.65 nM against P. carinii DHFR, 0.57 nM against M. avium DHFR, and 55 nM against rat DHFR. The potency of 13 against P. carinii DHFR was 20-fold greater than that of PTX (IC50 = 13 nM), and its selectivity index (SI) relative to rat DHFR was 85, whereas PTX was nonselective. The activity of 13 against P. carinii DHFR was 20 000 times greater than that of TMP, with an SI of 96, whereas that of TMP was only 14. However 13 was no more potent than PTX against M. avium DHFR, and its SI was no better than that of TMP. Molecular modeling dynamics studies using compounds 10 and 13 indicated a slight binding preference for the latter, in qualitative agreement with the IC50 data. Among the pteridines, the most potent against P. carinii DHFR and M. avium DHFR was the 2′-(5-carboxy-1-butynyl) dibenz[b,f]azepinyl derivative 20 (IC50 = 2.9 nM), whereas the most selective was the 2′-(5-carboxy-1-pentynyl) analogue 21, with SI values of > 100 against both P. carinii and M. avium DHFR relative to rat DHFR. The final compound, 2,4-diamino-5-[3′-(4-carboxy-1-butynyl)-4′-bromo- 5′-methoxybenzyl]pyrimidine (22), was both potent and selective against M. avium DHFR (IC50 = 0.47 nM, SI = 1300) but was not potent or selective against either P. carinii or T. gondii DHFR.