37259-88-4

Upstream product

• 41733-86-2 lasalocid benzyl ester 
• 67045-68-5 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester 
• 25999-20-6 lasalocid sodium 
• 73657-53-1 (2S)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butan-1-ol 
• 84911-92-2 (3RS,4S)-4-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>hexan-3-ol 
• 84911-91-1 (2R)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butanal 
• 31478-26-9 4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one 
• 75371-81-2 3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester 
• 73657-51-9 benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether 
• 73657-52-0 benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(3(R)-1,5-dioxo-4(S)-methylspiro<2.5>-6(R)-octyl)-2(S)-tetrahydrofuryl>butyl ether 
• 75371-80-1 2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester 
• 84985-06-8 benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether 
• 75371-88-9 3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid methyl ester 
• 84911-36-4 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-(trimethylsiloxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butan-1-ol 

Downstream Products

• 31478-26-9 4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one 
• 73657-54-2 2-Hydroxy-3-methyl-6-((R)-3-methyl-4-oxo-butyl)-benzoic acid 
• 103882-72-0 C₆H₇N*C₃₄H₅₄O₈ 

Relevant academic research and scientific papers

Chemical Degradation of Lasalocid: (A) The Mannich Reaction (B) Baeyer-Villiger Oxidation of the Retro-Aldol Ketone

Under Mannich reaction conditions (diethylamine and formaldehyde in toluene under reflux) lasalocid (1) undergoes a unique transformation in which the carboxyl group is replaced by a diethylaminomethyl group.The resulting Mannich base 2 was converted back to lasalocid, proving that none of the other chemical and stereochemical features of the molecule were disturbed.Like other phenolic Mannich bases, the one derived from lasalocid readily alkylated mercaptans.The known thermal and base-induced retro-aldol degradations of the lasalocid both produce a ketone fragment 9 containing the cyclic ether units.Baeyer-Villiger oxidation of this ketone afforded a carboxylic acid fragment which still contained these ether units.The normal regiochemistry involved in oxidizing this ketone (R-CH2-CO-CHR'R'' type ) was cleanly reversed by first converting it into the hydroxymethylidene derivative 10.

X-ray crystallographic, FT-IR and NMR studies as well as anticancer and antibacterial activity of the salt formed between ionophore antibiotic Lasalocid acid and amines

Two new complexes of the ionophore antibiotic Lasalocid acid (LAS) with phenylamine (PhA) and butylamine (BuA) were synthesized and their molecular structures were studied using single crystal X-ray diffraction and spectroscopic methods. In the solid state both amines are protonated and all NH3+ protons are hydrogen bonded to etheric, hydroxyl and carboxylic oxygen atoms of the LAS anion. In chloroform solutions the structure observed in the crystal of LAS-BuA complex is preserved and an equilibrium between the LAS-PhA complex and dissociated Lasalocid acid and phenylamine is observed. In vitro antimicrobial tests of the complexes showed a significant activity towards some strains of Gram-positive bacteria. For the first time Lasalocid acid and its complexes with amines were tested in vitro for cytotoxic activity against human cancer cell lines: A-549 (lung), MCF-7 (breast), HT-29 (colon) and mouse cancer cell line P-388 (leukemia). We found that LAS and its complexes are strong cytotoxic agents towards all tested cell lines. The cytostatic activity of the compounds studied is greater than that of cisplatin, indicating that Lasalocid and its complexes are promising candidates for new anticancer drugs.

Synthesis, FT-IR, 1H, 13C NMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic-Lasalocid acid and its complexes with Li+, Na+ and K+ cations

The polyether antibiotic Lasalocid acid has been converted to its Mannich base derivative by a chemoselective one-pot reaction with formaldehyde and morpholine through the decarboxylation process. Spectroscopic studies of the structure of this new derivative have shown that in this ortho-phenol Mannich base the OH...N intarmolecular hydrogen bond is present. The compound forms complexes with Li+, Na+ and K+ cations of exclusively 1:1 stoichiometry. The structures of these complexes have been studied and visualized by semi-empirical calculation based on results of spectrometric and spectroscopic investigation. It is demonstrated that in contrast to Lasalocid acid the novel Mannich type derivative forms preferential complexes with Li+ cation.

X-ray, spectroscopic and antibacterial activity studies of the 1:1 complex of lasalocid acid with 1,1,3,3-tetramethylguanidine

The crystal structure of the 1:1 complex between lasalocid acid (LAS) and 1,1,3,3-tetramethylguanidine (TMG) with one inclusion acetone molecule is studied by X-ray diffraction, FT-IR spectroscopy, 1H and 13C NMR. The complex is stabilized by three intra- and two inter-molecular hydrogen bonds formed between LAS anion and protonated TMG molecule. The NH2+ protons of the protonated TMG molecule are hydrogen bonded with the etheric oxygen atom O(6) and the hydroxyl oxygen atom O(8) of the LAS anion. The intermolecular NH?O hydrogen bonds are relatively long (2.933(4) ? and 2.903(4) ?). One oxygen atom of the carboxylate group is involved in a relatively strong intramolecular quasi-aromatic O(1)-H?O(3) hydrogen bond of 2.428(4) ? length, and the second oxygen atom in the bifurcated intramolecular relatively weak O(4)-H?O(2) of 2.803(4) ? and O(8)-H?O(2) of 2.805(4) ? hydrogen bonds. The O(4)-H?O(2) and O(8)-H?O(2) hydrogen bonds bind the ends of the LAS anion forming a pseudo-cyclic structure. The FT-IR spectra of the complex in the solid state and in the solution are comparable, thus the structures observed in the both states are also comparable. The in vitro biological tests of LAS-TMG show its good activity towards some strains of Gram-positive bacteria but this activity is lower than that of lasalocid acid.

Lasalocid acid as a lipophilic carrier ionophore for allylamine: Spectroscopic, crystallographic and microbiological investigation

A new complex of lasalocid acid with allylamine (LAS-AM) is synthesised and studied by X-ray, FT-IR, 1H NMR and 13C NMR, ESI MS methods. In the solid state allylamine is protonated and all protons of NH3+ are hy

Structural and spectroscopic studies of a new 2-naphthylmethyl ester of lasalocid acid

A new lasalocid 2-naphthylmethyl ester (NAFB) has been synthesised and studied by X-ray, 1H NMR, 13C NMR, FT-IR, UV-vis, fluorescence-spectroscopy as well as by the PM5 semiempirical method. The crystals of NAFB are monoclinic, space

Spectroscopic studies, crystal structures and antimicrobial activities of a new lasalocid 1-naphthylmethyl ester

A new lasalocid 1-naphthylmethyl ester (NAFA) has been synthesised and studied by X-ray, 1H NMR, 13C NMR, FT-IR, UV-vis, fluorescence as well as by PM5 semiempirical methods. The crystals of NAFA belong to the monoclinic system with the space group P21 with a = 13.4251(5) ?, b = 17.1064(7) ?, c = 18.5454(7) ?, β = 98.924(4)° and Z = 4. Two conformers of NAFA have been observed for two symmetry-independent molecules in different crystal environments. The molecular conformation of NAFA is partially stabilized by three intramolecular hydrogen bonds, in which the keto group is not involved. The FT-IR spectrum of NAFA in chloroform indicates that in this solvent the equilibrium between two structures of NAFA is realized. In one of the structures, the keto group is hydrogen bonded while in the other one this group is not involved in any hydrogen bond. The two structures of NAFA are discussed in detail. The new ester which has been additionally tested for its antimicrobial properties shows a certain activity against Gram-positive bacteria, however no activity against Gram-negative bacteria and Candida.

Stereoselective synthesis of polyether antibiotics, lasalocid A and isolasalocid A, via a chelation-controlled formation of tetrahydrofuran rings under thermodynamic conditions

The B-rings (2,5-trans-tetrahydrofurans) of lasalocid A (6) and isolasalocid A (7) were stereoselectively constructed from the corresponding p-methoxyphenylallyl alcohols (13a, 13b) by treatment with ZnBr2 to give C13-C24 fragments (14a, 14b) via a new chelation-controlled cyclization under thermodynamic conditions. After their conversion into lasalocid ketone (19) and BOM-isolasalocid ketone (20), coupling with the C1-C11 aldehyde (22) completed the synthesis of 6 and 7, respectively.

Total Synthesis of Polyether Antibiotics. Synthesis of the Enantiomer of Lasalocid A (X-537A)

A convergent total synthesis of the enantiomer of lasalocid A (X-537A) and the preliminary results of the biological testing of this compound are reported.