On March 29, 2007, Hashimoto, Kazuki; Nakamura, Tomoaki; Nakamura, Kei; Kurimoto, Ayumu; Isobe, Yoshiaki published a patent.Quality Control of Methyl 2-(3-formylphenyl)acetate The title of the patent was Preparation of novel adenine compounds having immunomodulating activity. And the patent contained the following:
Novel N-benzyl- and 9-(3-pyridyl)-7,8-dihydro-8-oxoadenine derivatives represented by the formula (I) [A1, A2 = each (un)substituted aromatic carbocycle or aromatic heterocycle; L4 = independently a single bond or linear or branched alkylene; X = O, S, SO, SO2, NH, or alkyl-N; L1, L2, L3 = single bond, alkylene, alkenylene, or alkynylene wherein any methylene group is optionally replaced with O, S, SO, SO2, CO, or each N-(un)substituted alkyl-(un)substituted NHCO, CONH, NHSO2, SO2NH, NHCO2, O2CNH, NHCONH, NHC(:NH)NH, or C(:NH)NH; R1 = halo, each (un)substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl; R2 = H or (un)substituted alkyl; R3 = each (un)substituted alkyl, alkenyl, alkynyl, cycloalkyl, saturated heterocyclyl, aryl, or heteroaryl; any methylene, methine, or imino group in L2 or L3 is bonded to R3 on the N atom adjacent to L2 an dL3 to form 4- to 7-membered N-containing heterocyclic ring] or pharmaceutically acceptable salts thereof were prepared The compounds have activity of activating Toll-like receptor (TLR7) and useful as immunomodulators for treating and/or preventing allergies, viral diseases, and cancers, in particular asthma, chronic obstructive pulmonary disease (COPD), allergic rhinitis, allergic conjunctivitis, atopic dermatitis, hepatitis B, hepatitis C, human immunodeficiency virus (HIV), human papillomavirus (HPV), bacterial infection, or dermatitis (no data). Thus, mesylation of 2-butoxy-9-[6-(4-hydroxybutoxy)pyridin-3-yl]-8-methoxyadenine by methanesulfonyl chloride in the presence of 4-dimethylaminopyridine and Et3N in THF at room temperature for 30 min followed by condensation with 2-(aminomethyl)phenylacetic acid Me ester in the presence of NaI and K2CO3 in DMF at 60° for 48 h gave 2-butoxy-8-methoxy-9-[6-[4-(3-methoxycarbonylmethylbenzyl)aminobutoxy]pyridin-3-ylmethyl]adenine which was stirred with a mixture of concentrated H2SO4 and MeOH and neutralized with 28% aqueous NH3 solution to give 2-butoxy-7,8-dihydro-9-(6-[4-(3-methoxycarbonylmethylbenzyl)aminobutoxy]pyridin-3-ylmethyl)-8-oxoadenine. II activated human TLR-7 in HEK293 cells with EC50 of 9.1 nM in a human TLR-7 reporter assay. The experimental process involved the reaction of Methyl 2-(3-formylphenyl)acetate(cas: 142327-44-4).Quality Control of Methyl 2-(3-formylphenyl)acetate
The Article related to dihydrooxoadenine preparation immunomodulator, pyridinylmethyldihydrooxoadenine benzyldihydrooxoadenine preparation immunomodulator, toll like receptor tlr7 activator dihydrooxoadenine preparation, allergy viral disease cancer treatment prevention dihydrooxoadenine preparation and other aspects.Quality Control of Methyl 2-(3-formylphenyl)acetate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics