34449-95-1Relevant articles and documents
Function-oriented synthesis of liponucleoside antibiotics
Tanino, Tetsuya,Yamaguchi, Mayumi,Matsuda, Akira,Ichikawa, Satoshi
supporting information, p. 1836 - 1840 (2014/04/03)
Function-oriented synthesis of a class of liponucleoside antibiotics was investigated through rational simplification guided by previous structure-activity relationship studies of caprazamycins and muraymycins to address the issue associated with their molecular complexity. A lactam-fused isoxazolidine scaffold was designed, and a diverse set of lactam-fused isoxazolidines derivatives were constructed by intramolecular 1,3-dipolar cycloaddition of alkenyl nitrones. Several analogues exhibited moderate activity against a range of Gram-positive drug-resistant bacterial pathogens.
Structure-activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines
Shrestha, Anurupa,Sil, Diptesh,Malladi, Subbalakshmi S.,Warshakoon, Hemamali J.,David, Sunil A.
supporting information; experimental part, p. 2478 - 2481 (2009/12/25)
We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)3-NH-(CH2) 4-NH2] and norspermidine [NH2-(CH2)3-NH-(CH2) 3-NH2] backbones, with the N-alkyl group being held constant at C16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues.
Production of 1-(3-hydroxy-propyl)-1,4-diazepane and 1,4-bis(3,4,5-trimethoxy-benzoyloxy)-propyl-diazepane derivatives thereof
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, (2008/06/13)
There is disclosed a process for the production of 1,4-bis-[3-(3,4,5-trimethoxybenzyloxy)-propyl]-diazepane which consists of first reacting 3-aminopropanol with acrylonitrile and subsequently reacting in aqueous solution with formaldehyde and hydrocyanic acid or with formaldehyde and an alkali cyanide in the presence of alkali hydrogen sulfite to form cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amine; hydrogenating the thus obtained reaction product in the presence of a hydrogenating catalyst and ammonia to 1 (3-hydroxy-propyl)-1,4-diazepane and reacting the latter compound for example with 3-halogen propanol or with allyl alcohol and introducing two 3,4,5-trimethoxy-benzoyl groups into the thus obtained reaction product by esterification.
