- AZETIDOBENZODIAZEPINE DIMERS AND CONJUGATES COMPRISING THEM FOR USE IN THE TREATMENT OF CANCER
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A compound of formula IV: as well as drug-linkers and conjugates comprising this compound, and the use of the conjugates in treating cancer.
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Page/Page column 68-69
(2020/10/09)
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- Azetidine-Containing Alkaloids Produced by a Quorum-Sensing Regulated Nonribosomal Peptide Synthetase Pathway in Pseudomonas aeruginosa
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Pseudomonas aeruginosa displays an impressive metabolic versatility, which ensures its survival in diverse environments. Reported herein is the identification of rare azetidine-containing alkaloids from P. aeruginosa PAO1, termed azetidomonamides, which are derived from a conserved, quorum-sensing regulated nonribosomal peptide synthetase (NRPS) pathway. Biosynthesis of the azetidine motif has been elucidated by gene inactivation, feeding experiments, and biochemical characterization in vitro, which involves a new S-adenosylmethionine-dependent enzyme to produce azetidine 2-carboxylic acid as an unusual building block of NRPS. The mutants of P. aeruginosa unable to produce azetidomonamides had an advantage in growth at high cell density in vitro and displayed rapid virulence in Galleria mellonella model, inferring functional roles of azetidomonamides in the host adaptation. This work opens the avenue to study the biological functions of azetidomonamides and related compounds in pathogenic and environmental bacteria.
- Hong, Zhilai,Bolard, Arnaud,Giraud, Caroline,Prévost, Sébastien,Genta-Jouve, Grégory,Deregnaucourt, Christiane,H?ussler, Susanne,Jeannot, Katy,Li, Yanyan
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supporting information
p. 3178 - 3182
(2019/01/19)
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- FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
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Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.
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Paragraph 00169
(2017/03/08)
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- Synthesis of a Bicyclic Azetidine with in Vivo Antimalarial Activity Enabled by Stereospecific, Directed C(sp3)-H Arylation
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The development of new antimalarial therapeutics is necessary to address the increasing resistance to current drugs. Bicyclic azetidines targeting Plasmodium falciparum phenylalanyl-tRNA synthetase comprise one promising new class of antimalarials, especially due to their activities against three stages of the parasite's life cycle, but a lengthy synthetic route to these compounds may affect the feasibility of delivering new therapeutic agents within the cost constraints of antimalarial drugs. Here, we report an efficient synthesis of antimalarial compound BRD3914 (EC50 = 15 nM) that hinges on a Pd-catalyzed, directed C(sp3)-H arylation of azetidines at the C3 position. This newly developed protocol exhibits a broad substrate scope and provides access to valuable, stereochemically defined building blocks. BRD3914 was evaluated in P. falciparum-infected mice, providing a cure after four oral doses.
- Maetani, Micah,Zoller, Jochen,Melillo, Bruno,Verho, Oscar,Kato, Nobutaka,Pu, Jun,Comer, Eamon,Schreiber, Stuart L.
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supporting information
p. 11300 - 11306
(2017/08/21)
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- NEW TETRACYCLINE DERIVATIVES AS ANTIINFECTIVE AGENTS
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In accordance with one embodiment, the present invention provides a compound of general formula (I), stereoisomers thereof and/or its pharmaceutically acceptable salts thereof, which have antibacterial activity; with methods of treating infectious diseases in warm blooded animals employing these new compounds.
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Page/Page column 34
(2009/04/25)
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- N-(5-MEMBERED AROMATIC RING)-AMIDO ANTI-VIRAL COMPOUNDS
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Disclosed are compounds having Formula (I) and the compositions and methods thereof for treating or preventing a viral infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R2, m, R, V, W, T, Z, R
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Page/Page column 96
(2008/06/13)
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- 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS
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The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent "chemoattractant receptor-homologous molecule expressed on Th2 cells" antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.
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Page/Page column 172-173
(2010/10/20)
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- Synthesis of a new precursor to the nicotinic receptor tracer 5-IA-85380 precursor using trimethylsilyl iodide as deblocking agent
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We describe the synthesis of a new precursor of 5-IA-85380, specific radiotracer for α4β2 nicotinic acetylcholine receptors. (S)-5-Trimethylstannyl-3-(2-azetidinylmethoxy)pyridine (4) was prepared in six steps and 62% overall yield starting from (S)-2- azetidinecarboxylic acid. The key step of this synthesis is selective release of the amine function without removing the stannyl moiety using trimethylsilyl iodine.
- Brenner, Eric,Baldwin, Ronald M.,Tamagnan, Gilles
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p. 3607 - 3610
(2007/10/03)
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- Process for preparation of optically active n-substituted azetidine-2-carboxylic acids
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The object of the present invention is to produce an optically active N-substituted azetidine-2-carboxylic acid by an efficient, expedient and commercially profitable process. The present invention provides a production method of an optically active N-sub
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- Neurotrophic 2-azetidinecarboxylic acid derivatives, and related compositions and methods
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This invention provides compounds having the following general structure: This invention also provides pharmaceutical compositions comprising same and methods of using these compositions to treat and prevent disorders characterized by neuronal damage.
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- Synthesis of chiral bicyclic azetidine derivatives
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(2S)-N-Benzoyl-2-azetidinecarboxylic acid was converted into several derivatives of (5R)-1-azabicycloheptane via lactamization of 3-((2R)-azetidine)propanoic acid, subsequent aldol reaction and reduction. The structures of three stereoisomers of (5R)-3-(hydroxy-(4-nitrophenyl)methyl)-1-azabicyclo[3.2.0]heptan-2-one were determined by X-ray crystallography.
- Barrett, Anthony G. M.,Dozzo, Paola,White, Andrew J. P.,Williams, David J.
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p. 7302 - 7314
(2007/10/03)
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- PROCESS FOR PREPARATION OF OPTICALLY ACTIVE N-SUBSTITUTED AZETIDINE-2-CARBOXYLIC ACIDS
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The object of the present invention is to produce an optically active N-substituted azetidine-2-carboxylic acid by an efficient, expedient and commercially profitable process. The present invention provides a production method of an optically active N-sub
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- Processes for producing azetidine-2-carboxylic acid and intermediates thereof
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PCT No. PCT/JP98/01895 Sec. 371 Date Dec. 30, 1999 Sec. 102(e) Date Dec. 30, 1999 PCT Filed Apr. 24, 1998 PCT Pub. No. WO98/47867 PCT Pub. Date Oct. 29, 1998The present invention has its object to provide a process for producing azetidine-2-carboxylic acid and an intermediate thereof, which is efficient and economical and suited for industrial practice. The present invention is related to a process for producing azetidine-2-carboxylic acid of the following formula (5), which comprises subjecting a 4-oxo-2-azetidinecarboxylic acid derivative represented by the general formula (1) to hydride reduction to give azetidine-2-methanol of the following formula (2), treating the same with an amino-protecting agent to give N-protected azetidine-2-methanol represented by the following general formula (3), treating this with an oxidizing agent to give N-protected azetidine-2-carboxylic acid represented by the following general formula (4) and, further, subjecting the amino-protecting group thereof to elimination.
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- Total Synthesis of Mugineic Acid. Efficient Use of the Phenyl Group as the Carboxyl Synthon
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Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6).The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.
- Matsuura, Fumiyoshi,Hamada, Yasumasa,Shioiri, Takayuki
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p. 8211 - 8222
(2007/10/02)
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- Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole
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Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.
- Rama Rao,Gurjar,Kaiwar
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p. 859 - 862
(2007/10/02)
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- Efficient Synthesis of Mugineic Acid, A Typical Phytosiderophore, Utilizing the Phenyl Group as the Carboxyl Synthon
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Stereoselective total synthesis of mugineic acid, a unique phytosiderophore from roots of barley, has been achieved from (2R,3R)- and (2S,3S)-2,3-epoxycinnamyl alcohols employing the phenyl group as the carboxyl synthon.
- Matsuura, Fumiyoshi,Hamada, Yasumasa,Shioiri, Takayuki
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p. 7917 - 7920
(2007/10/02)
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