The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: H-Trp-OMe.HCl( cas:7524-52-9 ) is researched.SDS of cas: 7524-52-9.El Rayes, Samir M.; Ali, Ibrahim A. I.; Fathalla, Walid; Mahmoud, Mostafa A. A. published the article 《Synthesis, molecular docking and biological evaluation of some new benzotriazines》 about this compound( cas:7524-52-9 ) in International Electronic Conference on Synthetic Organic Chemistry, 23rd, Nov. 15-Dec. 15, 2019. Keywords: benzotriazinone hydrazide dipeptide amide preparation antibacterial antitumor docking. Let’s learn more about this compound (cas:7524-52-9).
Me 2-(4-oxobenzotriazin-3(4H)-yl)alkanoates I [X = CH2, CH2CH2, CH(i-Pr); X1 = MeO] proved to be important intermediates for the preparation of some biol. interesting compounds containing the benzotriazinone ring system. The above compounds were prepared by direct diazotization of Me anthranilate followed by addition of amino acid esters hydrochloride in a one-pot strategy. An equivocal synthesis of compound I (X = CH2; X1 = MeO) was achieved by alkylation of benzotriazin-4(3H)-one with Me chloroacetate. A series of N-alkyl-2-(4-oxobenzotriazin-3(4H)-yl) alkanamides I (X = CH2, CH2CH2; X1 = NR1R2; R1 = i-Pr, n-Bu, t-Bu, cyclohexyl, etc., R2 = H; R1R2N = 1-piperidinyl, 4-morpholinyl) and Me 2-(2-(4-oxobenzotriazin-3(4H)-yl)alkanamido)alkanoates (dipeptides) I [X = CH2, CH2CH2; X1 = NHR3; R3 = MeO2CCH2, MeO2CCH(i-Bu), MeO2C(CH2)3, MeO2CCH(indol-3-ylmethyl)] were prepared via azide coupling from compounds I (X = CH2, CH2CH2; X1 = MeO). Esters I (X = CH2, CH2CH2; X1 = MeO) were converted into the corresponding hydrazides followed by condensation with aldehydes, such as 4-methoxybenzaldehyde, 4-dimethylaminobenzaldehyde and arabinose, to afford the corresponding hydrazone derivatives. All the synthesized compounds were subjected to the mol. docking using MOE 2008-10 software as agonists for E. coli Fab-H receptor and Vitamin D receptor for antibacterial and anticancer evaluation, resp. The most pronounced strong binding affinity towards the target E. coli Fab-H receptor was shown by the parent benzotriazin-4(3H)-one and compounds I [X = CH2, X1 = i-PrNH; X = CH2CH2, X1 = MeO2CCH2, MeO2C(CH2)3; X = CH2, X1 = 4-MeOC6H4CH:NN, 4-Me2NC6H4CH:NN; X = CH2CH2, X1 = 4-Me2NC6H4CH:NN]. On the other hand, the most pronounced strong binding affinity towards the target Vitamin D receptor were benzotriazin-4(3H)-one and compounds I [X = CH2, X1 = MeO2C(CH2)3; X = CH2CH2, X1 = MeO2CCH(indol-3-ylmethyl); X = CH2, X1 = 4-MeOC6H4CH:NN]. The in-vitro antibacterial activity of highest binding affinity docked compounds were tested against E. coli, Staphylococcus aureus and Salmonella spp. All the tested compounds gave effective pos. results against E. coli with inhibitory zone of about 1.1 cm, while were inactive against Staphylococcus aureus and Salmonella spp. The in-vitro cytotoxic activity of the highest binding affinity docked compounds were tested against human liver carcinoma cell line (HepG2) cancer cell lines. Many compounds showed potent cytotoxic activity with low IC50 values, especially benzotriazin-4(3H)-one (6.525μM) and I (X = CH2; X1 = 4-MeOC6H4CH:NN) (10.97μM) compared to standard drug doxorubicin (5.8μM).
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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem