93860-66-3Relevant academic research and scientific papers
From the production of amphetamine phenylpropanolamine
-
Page/Page column 18-19, (2008/06/13)
A process for making compound of formula Ifrom a phenylpropanolamine salt of formula IIwherein:R1 is hydrogen or a lower alkyl group;each R2 is independently a hydrogen, halogen, lower alkyl group, lower alkoxy groups, lower alkyl group substituted with 1 to 5 halogens, lower alkoxy groups substituted with 1 to 5 halogens, or both R2 together when on adjacent carbons constitute a -O(CH2)xO- where x is 1 to 4, thereby forming a ring structure fused with the phenyl group;R3 is a C1-C8-alkyl group, a C1-C12-aralkyl group, C1-C12-alkaryl group, or a phenyl group, each optionally substituted by 1 to 5 substituents selected from halogen, hydroxy, or C1-C6-alkyl; andHX is an equivalent of an organic or inorganic acid,the process comprising:(a) acylating the phenylpropanolamine salt of formula II with an acylating agent in a solvent at elevated temperature to make a reaction mixture containing an O-acylated phenylpropanolamine salt of formula III which can be isolated by the addition of a crystallization solvent, or optionally this mixture can be used in the next step; and(b) hydrogenating the O-acylated phenylpropanolamine salt to make the compound of formula I in the presence of a catalyst.
Chiral DNA gyrase inhibitors. 3. Probing the chiral preference of the active site of DNA gyrase. Synthesis of 10-fluoro-6-methyl-6,7-dihydro-9- piperazinyl-2H-benzo[a]quinolizin-20-one-3-carboxylic acid analogues
Fecik, Robert A.,Devasthale, Pratik,Pillai, Segaran,Keschavarz-Shokri, Ali,Shen, Linus,Mitscher, Lester A.
, p. 1229 - 1236 (2007/10/03)
In pursuit of an apparent literature anomaly, S- and R-6-methyl-6,7- dihydro-2H-benzo[a]-quinolizin-2-one-3-carboxylic acids (12 and 22) were synthesized by an unambiguous route from optically active norephedrines, and their antibacterial potencies were measured. Against Gram-negative microorganisms and DNA gyrase a preference for S-absolute configuration was found whereas R-absolute stereochemistry was more active against Gram-positives. These results are in partial conflict with an earlier report. In an attempt to enhance potency, racemic 10-fluoro-9-piperazinyl (35) and related analogues were synthesized by a novel route. The latter analogues were surprisingly unimproved in potency. The implications of these findings are briefly discussed.
Aeruginoguanidines 98-A-98-C: Cytotoxic unusual peptides from the cyanobacterium Microcystis aeruginosa
Ishida, Keishi,Matsuda, Hisashi,Okita, Yuji,Murakami, Masahiro
, p. 7645 - 7652 (2007/10/03)
Aeruginoguanidines 98-A-98-C (1-3) were isolated from the cyanobacterium Microcystis aeruginosa (NIES-98). The structures of aeruginoguanidines 98-A-98-C (1-3) were determined by two-dimensional 1H-1H and 1H-13C NMR correlation experiments and confirmed by mass spectral analysis. The absolute stereochemistry of 1, consisting of Hphpa trisulfate (1-(4-hydroxy-3-hydroxymethyl)phenyl-1-hydroxy-2-propylamine 4′,3′,1-tri-O-sulfate), MpArg (Nα-methyl-Nω-prenylarginine) and MgArg ((Z)-Nα-methyl-Nω-geranylarginine), was determined by the NMR analyses of phenylglycine methyl ester (PGME) or Boc phenylglycine (BPG) derivatives of acid hydrolysates. These compounds showed moderate cytotoxicity against the P388 murine leukemia cells.
MISE EN EVIDENCE PAR RMN-(1)H ET -(13)C D'ISOMERISME Z/E ET D'EQUILIBRE CONFORMATIONNEL SUR UNE SERIE DE DERIVES MONO- ET DIACETYLES DE 2-ALKYLAMINO-1-PHENYLPROPAN-1-OLS
Tytgat, D.,Gelbcke, M.
, p. 479 - 490 (2007/10/02)
(1)H- and (13)C NMR studies of mono- and diacetylated-erythro- and threo-2-alkylamino-1-phenylpropan-1-ols, C6H5CHOHCHNHRCH3 (R = H, CH3, C2H5 AND i-C3H7) show that the series exhibit Z/E isomerism about the C-N amide bond.The Z/E ratio increases in the monoacetylated series CH3 1-C2 and N-C2 bonds.In the Z configuration, the conformer Z-s-syn where the proton H-2 is syn with the N-alkyl substituent predominates.
