Folic acid ester

Pyrimidinopyrazines related to folic acid have been investigated in some detail for their antimeta-bolic and antineoplastic activities. A related compound, which lacks one nitrogen atom, has been described as an antiproliferative agent, indicating it too has an effect on cell replication. Aldol condensation of the benzaldehyde 99 with ethyl acetoacetate gives the cinnamate 100. This is then reduced catalytically to the acetoacetate 101. Reaction of that keto ester with 2,4,6- triami-nopyrimidine gives the product 102 which is subsequently chlorinated (103) and subjected to hydrogenolysls. There is thus formed piritrexim (104) [17]. 

L-Tetrahydrofolic acid is a versatile intermediate for the manufacture of various folates, e.g., L-leucovorin [19], which is used in cancer therapy, or Metafolin , which is used as a vitamin in functional food. To our knowledge optically pure L-tetrahydrofolic acid is still obtained by repeated fractional crystallization from an equimolar mixture of diastereoisomers formed by nondiastereoselective hydrogenation of folic acid. In order to increase the yield of l-tetrahydrofolic acid and to avoid recrystallization steps, we checked the utility of our ligand for the diastereoselective hydrogenation of folic acid dimethyl ester benzenesulfonate (Scheme 1.4.4). 

Scheme 1.4.4 Hydrogenation of folic acid dimethyl ester benzenesulfonate.

I 7.4 The Daniphos" Ligands Synthesis and Catalytic Applications Table 1.4.3 Results of the hydrogenation of folic acid dimethyl ester. 

The life cycle of Dictyostelium discoideum is described briefly in Box 11-C. About 105 individual amebas aggregate to form a moving "slug" in response to the chemoattractant cAMP. Some other species of Dictyostelium are attracted to a folic acid derivative or to the ethyl ester of N-propionyl-y-L-glutamyl-L-omithine-5-lactam 226... 

Chnirnagcrt FORTE Fcrructlc] (elemental iron) 4 ferrous fumsitatc (demerit iron). Ester-C . vitamin It it (cyanocohalamin), and Folic Acid Soybean Oil. yellow beeswax Lecithin... 

A different type of modification in Region E was achieved [223, 224] in the form of the MTX analogue (VI.8) and the folic acid analogue (VI. 10), in which NH is inserted between the phenyl and CONH moiety. For the synthesis of (VI.8), 4-amino-4-deoxy-V °-methylpteroic acid was treated with diphenyl-phosphoryl azide in DMSO, the resultant azide ((VI. 12), 87% yield) was photolyzed in DMF solution in the presence of dimethyl L-glutamate to obtain dimethyl ester (VI.9) (51% yield), and (VI.9) was hydrolyzed with 0.1 M... 

An unexpected feature of the chemistry of the above ureido ester analogues was the apparent ease with which they underwent at least partial racemization at the a-carbon during alkaline hydrolysis to ureido acids. Support for the conclusion that racemization was taking place came from a combination of direct polarometric measurements on the ureido diacids (low rotation in comparison with MTX and folic acid) and indirect evidence that hydrolysis was proceeding via a hydantoin intermediate. Thus, when the ester (VI.9) was heated in MeOH or CHCI3 in the presence of the strong organic base l,5-diazabicyclo[3.4.0]non-5-ene, a product formed in 61% yield which was tentatively identified as (VI.15). Alkaline hydrolysis of (VI.15) yielded (VI.8). 

Am i no-9,10-dihydro-9,10-dioxo-4((3-((2-(sulfooxy) ethyl) sulfonyl) phenyl)-amino)-2-anthracenesulfonic acid, disodium salt 1-Amino-9,10-dihydro-4-(m-((2-hydroxyethyl) sulfonyl) anilino-9,10-dioxo-2-anthracenesulfonic acid, hydrogen sulfate (ester), disodium salt. See Reactive blue 19 N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl) methyl] amino] benzoyl]-L-glutamic acid. See Folic acid... 

Vitamin Bi (thiamine), B2 (riboflavin). Be (pyridoxine), B12 (cyanocobalamine), C (ascorbic acid), E (tocopherols), folic acid, pantothenic acid, K, K2, K3 (menadione), PP factor (nicotinamide), biotin Benzimidazole drugs, bromoisovalerylurea, cardiazol, chlorhexidine, dicoumarol, dulcin, isoniazid, 2-nitrofuran derivatives, parabens (4-hydroxybenzoic acid esters), phenacetin, phenylbutazone (and its metabolite oxyphenbutazone), propipocaine, quercetin, rutin, thiomersal (sodium ethylmercurithiosalicylate)... 

Uses sun-screening agent in cosmetics, moisturizers, shampoos, hair-care products, nail polish, lipstick, lip balms, oral vitamin supplements manufacture of various esters (local anesthetics), folic acid and azo dyes in sunburn preventatives used in laboratories as sulfonamide antagonist antirickettsial Cross para groups of compounds. PA PABA A... 

Vitamin A (Retinol) and Vitamin A acid (Tretinoin) are different substances and cannot be used instead of each other because they have a different pharmacotherapeutic application. Folic acid (Acidum foUcum) and FoUnic acid (Acidum folinicum) are closely related substances but differ significantly in effective strength. Tocopherol esters are applied as vitamin E tocopherol itself is especially applied as antioxidant. 

---