254763-27-4Relevant academic research and scientific papers
Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis
Hu, Fang,Zhang, Yan-Hong,Yao, Zhu-Jun
, p. 3511 - 3515 (2007)
Three new diastereomeric shikimic acid analogues (4-amino-3,5-dihydroxyl-cyclohex-1-en-carboxylic acids, 16) bearing a C-4 amino group were synthesized in parallel by a mixture-operation protocol. Ring-closing enyne metathesis (RCEYM) under ethylene atmos
CYCLIC PEPTIDE ANTIBIOTICS
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Paragraph 00286; 00335, (2020/09/27)
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.
Total Syntheses and Biological Activities of Vinylamycin Analogues
Bai, Fang,Chen, Yue,Ding, Yahui,Guo, Xiaoqian,Jiang, Shende,Kuang, Beijia,Li, Chun-Qi,Li, Jiangnan,Li, Luyuan,Liu, Jianwei,Liu, Ying,Wang, Jinghan,Wang, Liang,Xia, Bo,Yang, Guang,Zhang, Quan,Zhu, Xiao-Yu
, p. 1189 - 1209 (2017/02/19)
Natural depsipeptide vinylamycin was reported to be an antibiotic previously. Herein we report vinylamycin to be active against K562 leukemia cells (IC50 = 4.86 μM) and be unstable in plasma (t1/2 = 0.54 h). A total of 24 vinylamycin analogues with modification of the OH group and chiral centers were generated via a combinatorial approach. The lead compound 1a was subsequently characterized as having the following: no antimicrobial activity, significantly higher plasma stability (t1/2 = 14.3 h), improved activity against K562 leukemia cells (IC50 = 0.64 μM), and up to 75% cell inhibition without significant toxicities in K562 cells xenograft zebrafish model. Furthermore, compound 1a maintained its activity against the breast cancer cell line MCF-7 under hypoxic conditions. In comparison, the activity of gemcitabine in the same hypoxic in vitro model of MCF-7 cells was 15-fold lower. Therefore, the present results demonstrate that 1a has great potential as an anticancer agent.
MACROCYCLIC LRRK2 KINASE INHIBITORS
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Page/Page column 178, (2016/04/09)
The present invention relates to novel macrocyclic compounds of formula (I) and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of LRRK2 (Leucine-Rich Repeat Kinase 2). Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine or diagnostic agent, in particular for the treatment and/or diagnosis of diseases characterized by LRRK2 kinase activity such as neurological disorders including Parkinson's disease and Alzheimer's disease.
SULFONAMIDES AS HIV PROTEASE INHIBITORS
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Page/Page column 44-46, (2012/05/19)
Compounds of Formula I are disclosed: wherein L, A, R1, R2, R3A, R3B, R4A, R4B, R5, R6 and R7 are defined herein. The compounds encompassed by Formula I include compounds which are HIV protease inhibitors and other compounds which can be metabolized in vivo to HW protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines
Total synthesis of (-)-aplaminal
Smith III, Amos B.,Liu, Zhuqing
supporting information; experimental part, p. 4363 - 4365 (2009/06/06)
(Chemical Equation Presented) The total synthesis and assignment of absolute configuration of (-)-aplaminal (1), a cytotoxic metabolite from a sea hare possessing a triazobicyclo[3.2.1]octane skeleton, has been achieved. The synthesis entailed condensatio
Efficient tin hydride-mediated radical cyclisation of secondary amides leading to substituted pyrrolidinones. Part 2. Application to the synthesis of aromatic kainic acid analogues
Bryans, Justin S.,Large, Jonathan M.,Parsons, Andrew F.
, p. 2905 - 2910 (2007/10/03)
An enantioselective synthesis of phenyl allokainoid, starting from D-serine, is reported. Tin-mediated cyclisation of a secondary amide was used in the key step to produce a trisubstituted pyrrolidinone in excellent yield (ca. 80%). The predominant format
Efficient radical cyclisation of secondary amides: An enantioselective synthesis of phenyl allokainoid
Bryans, Justin S.,Large, Jonathan M.,Parsons, Andrew F.
, p. 3487 - 3490 (2007/10/03)
Cyclisation of various unsaturated haloamides with tributyltin hydride/AIBN has been explored. Substituted pyrrolidinones were isolated in good to excellent yield and the cyclisation of a serine-derived amide was utilised as the key step in an enantiosele
The synthesis of 4,5-methano congeners of α-kainic and α-allo-kainic acids as probes for glutamate receptors
Hanessian, Stephen,Ninkovic, Sacha,Reinhold, Ulrich
, p. 8971 - 8974 (2007/10/03)
The synthesis of diastereomeric 4,5-methano-L-proline 3-acetic acids is described starting from D-serine. The key reactions include a free-radical carbocyclization and an acid-catalyzed destannylative cyclopropanation of an iminium ion intermediate. Copyright (C) 1996 Elsevier Science Ltd.
Total Synthesis of Balanol and Designed Analogues
Nicolaou, K. C.,Koide, Kazunori,Bunnage, Mark E.
, p. 454 - 466 (2007/10/03)
The total synthesis of balanol, a potent protein kinase C inhibitor isolated from the fungus Verticillium balanoides, is described.The hexahydroazepine fragment was prepared from D-serine through a sequence of reactions including the diastereoselective allylboration of a derived amino aldehyde and a base-induced 7-exo-tet ring closure as key steps.The benzophenone fragment was secured through the initial coupling of the two functionalised aromatic components through an ester linkage, followed by intramolecular nucleophilic attack of an aryl lithium derivative to form the desired ketone bridge.After coupling of the two balanol domains, the adoption of benzyl-derived protecting groups for the latent functionalities then allowed the liberation of balanol in a single step by catalytic hydrogenolysis.Finally, the newly developed synthetic strategy was applied to the synthesis of a variety of designed balanol analogues for biological evaluation. - Keywords: antitumor agents, balanol, enzyme inhibitor, natural product, total synthesis
