113707-74-7Relevant academic research and scientific papers
Optimization of globomycin analogs as novel gram-negative antibiotics
Braun, Marie-Gabrielle,Burdick, Daniel J.,Castanedo, Georgette M.,Chen, Yi-Chen,Cheng, Yun-Xing,Cheong, Jonathan,Daniels, Blake,Deshmukh, Gauri,Fu, Yuhong,Garland, Keira,Gibbons, Paul,Gloor, Susan L.,Hanan, Emily J.,Hua, Rongbao,Kapadia, Sharookh B.,Labadie, Sharada,Liu, Xiongcai,Pantua, Homer,Pastor, Richard,Stivala, Craig,Xu, Min,Xu, Yiming,Zheng, Hao
supporting information, (2020/08/13)
Discovery of novel classes of Gram-negative antibiotics with activity against multi-drug resistant infections is a critical unmet need. As an essential member of the lipoprotein biosynthetic pathway, lipoprotein signal peptidase II (LspA) is an attractive target for antibacterial drug discovery, with the natural product inhibitor globomycin offering a modestly-active starting point. Informed by structure-based design, the globomycin depsipeptide was optimized to improve activity against E. coli. Backbone modifications, together with adjustment of physicochemical properties, afforded potent compounds with good in vivo pharmacokinetic profiles. Optimized compounds such as 51 (E. coli MIC 3.1 μM) and 61 (E. coli MIC 0.78 μM) demonstrate broad spectrum activity against gram-negative pathogens and may provide opportunities for future antibiotic discovery.
CYCLIC PEPTIDE ANTIBIOTICS
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Paragraph 00415, (2019/04/11)
Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of lipoprotein signal peptidase II (LspA), a key protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.
Reagent-controlled diastereoselective synthesis of (2S,3R)- and (2R,3R)-2,3-diaminobutanoic acid derivatives using proline-catalyzed α-hydrazination reaction
Makino, Kazuishi,Kubota, Sayaka,Hara, Sousuke,Sakaguchi, Masaru,Hamajima, Akinari,Hamada, Yasumasa
experimental part, p. 9468 - 9473 (2009/12/28)
(2S,3R)- and (2R,3R)-2,3-Diaminobutanoic acid (Dab) derivatives were efficiently synthesized from Cbz-(R)-alanine using the proline-catalyzed diastereoselective α-hydrazination reaction and the SmI2-promoted reductive cleavage of the N-N bond a
SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS
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Page/Page column 100, (2009/04/25)
Disclosed are compounds of formula (I) which are bradykinin B1 receptor (B1R) antagonists. These compounds are useful to treat diseases or relieve adverse symptoms associated with inflammation and pain. The invention encompasses novel compounds and acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases involving inflammation and pain.
Absolute configuration of the solenopsins, venom alkaloids of the fire ants
Leclercq,Thirionet,Broeders,Daloze,Vander Meer,Braekman
, p. 8465 - 8478 (2007/10/02)
An effective and practical procedure has been developed that allows the assignment of the absolute configuration of solenopsins from diverse origins using only small amounts of material. The method is based on the transformation of the natural secondary amines into diastereoisomeric amides by reaction with (R)-2-methoxy-2-phenyl-2-(trifluoromethyl)acetic acid chloride (MTPA-Cl), followed by comparison of their chromatographic behaviour with those of standards of established absolute configuration. This procedure has been applied to three samples of ants: Solenopsis geminata workers, S. invicta workers and S. invicta alates. It has been found that the absolute configuration of the trans alkaloids is always (2R,6R) while that of the cis alkaloids is (2R,6S). Moreover, a new synthesis of enantiomerically pure solenopsin A (4) and isosolenopsin A (3) starting from L-alanine is presented.
THE SYNTHESIS OF EITHER (+) OR (-) TRANS-2,5-DIMETHYLPYRROLIDINE
Schlessinger, Richard H.,Iwanowicz, Edwin J.
, p. 2083 - 2086 (2007/10/02)
Trans-2,5-dimethylpyrrolidine, in either optical series, is prepared starting from D or L-alanine in an efficient and reasonably brief reaction sequence.
