79722-22-8

Upstream product

• 19689-97-5 N-(tert-butoxycarbonyl)-N-methylhydroxylamine 
• 100-39-0 benzyl bromide 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 622-33-3 N-benzyloxyamine 
• 79722-21-7 tert-butyl N-(benzyloxy)carbamate 
• 74-88-4 methyl iodide 

Downstream Products

• 19689-97-5 N-(tert-butoxycarbonyl)-N-methylhydroxylamine 
• 117679-85-3 4-((benzyloxy)(methyl)amino)-4-oxobutanoic acid 
• 71925-14-9 O-benzyl-N-methylhydroxylamine hydrochloride 
• 79722-20-6 O-benzyl N-methyl-N^α-(tert-butoxycarbonyl)-N^α-methyl-L-alaninehydroxamate 

Relevant academic research and scientific papers

Identification and Characterization of AES-135, a Hydroxamic Acid-Based HDAC Inhibitor That Prolongs Survival in an Orthotopic Mouse Model of Pancreatic Cancer

Pancreatic ductal adenocarcinoma (PDAC) is an aggressive, incurable cancer with a 20% 1 year survival rate. While standard-of-care therapy can prolong life in a small fraction of cases, PDAC is inherently resistant to current treatments, and novel therapies are urgently required. Histone deacetylase (HDAC) inhibitors are effective in killing pancreatic cancer cells in in vitro PDAC studies, and although there are a few clinical studies investigating combination therapy including HDAC inhibitors, no HDAC drug or combination therapy with an HDAC drug has been approved for the treatment of PDAC. We developed an inhibitor of HDACs, AES-135, that exhibits nanomolar inhibitory activity against HDAC3, HDAC6, and HDAC11 in biochemical assays. In a three-dimensional coculture model, AES-135 kills low-passage patient-derived tumor spheroids selectively over surrounding cancer-associated fibroblasts and has excellent pharmacokinetic properties in vivo. In an orthotopic murine model of pancreatic cancer, AES-135 prolongs survival significantly, therefore representing a candidate for further preclinical testing.

Phosphonodiamidate prodrugs of N-alkoxy analogs of a fosmidomycin surrogate as antimalarial and antitubercular agents

A series of N-alkoxy analogs of a L-leucine ethyl ester phosphonodiamidate prodrug of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. These compounds originate b

Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents

Two classes of prodrugs of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. To this end, a novel efficient synthesis route was developed involving a cross metathe

Studies at the ionizable position of cephalosporins and penicillins: Hydroxamates as substitutes for the traditional carboxylate group

Classically, β-lactams need an ionizable group to potentiate antibacterial activity. Sets of cephalosporins and penicillins featuring different substituted hydroxamates in place of the traditional carboxylate group have been synthesized and tested for antibiotic activity. Many of the compounds exhibited anti-bacterial activities with notable MIC values in the range of 6-0.2 μM.

Structural Requirements of Histone Deacetylase Inhibitors: SAHA Analogs Modified on the Hydroxamic Acid

Histone deacetylase (HDAC) proteins have emerged as targets for anti-cancer therapeutics, with several inhibitors used in the clinic, including suberoylanilide hydroxamic acid (SAHA, vorinostat). Because SAHA and many other inhibitors target all or most o

Biomimetic ferrichrome: Structural motifs for switching between narrow- and broad-spectrum activities in P. putida and E. coli

A series of novel ferrichrome (FC) analogs was designed based on the X-ray structure of FC in the FhuA transporter of Escherichia coli. Two strategies were employed: the first strategy optimized the overall size and relative orientation of H-bonding inter

Condensed derivatives of imidazole useful as pharmaceuticals

The invention relates to the compounds (I) and their acids and bases salts: wherein: the dotted line indicates a double bond; X is N or C-R1 and Y is N or C-R2, X and Y not being simultaneously N; A is selected from the group consisting of phenyl, naphthyl and (5-11) membered monocyclic or bicyclic unsaturated cycle or heterocycle possibly substituted as defined in the application, and A can also comprise either a further (4-7) membered heterocycle, said heterocycle being a monocycle, fused, saturated or unsaturated, the polycyclic system then comprising up to 14 members and up to 5 heteroatoms selected from N, O and S; B is Hydrogen or a substituent as defined in the application, or B is a (4-10) membered mono or bicyclic saturated or unsaturated heterocycle containing 1-3 heteroatoms selected from N, O and S, and possibly substituted as defined in the application; B not being Hydrogen when X is N and Y is C-R2; R1 is Hydrogen or a substituent as defined in the application; B and R1 cannot be simultaneously Hydrogen; R2 is Hydrogen or Halogen; their preparation, their use in the antibacterial prevention and therapy, alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.

Stability studies of hydrazide and hydroxylamine-based glycoconjugates in aqueous solution

Glycoconjugates can be readily formed by the condensation of a free-reducing terminus and a strong α-effect nucleophile, such as a hydrazide or a hydroxylamine. Further characterization of a series of glycoconjugates formed from xylose, glucose and N-acet

Significance of hydrogen bonding at the S1′ subsite of calpain I

α-Ketohydroxamates were synthesized as bioisosteres of α-ketoamides. The α-ketohydroxamates were generally more potent than the corresponding α-ketoamides. The potency of the compounds suggests that hydrogen bonding and steric bulk of substituents on the nitrogen atom of the ketoamide moiety influence calpain inhibition.

Acyclic oxyiminium ions. Mannich reactions and addition of grignard reagents

Acyclic oxyiminium ion generation from secondary hydroxylamines (4a,b and 6a,b) and formaldehyde in the presence of acetic acid is reported. Trapping these electrophiles with 2-methyl furan, pyrrole or indole affords a series of novel O-benzyl tertiary hydroxylamines in good to excellent yield. Benzotriazole mediated synthetic methodology has also been successfully developed to generate oxyiminium ions which react with Grignard reagents, to give novel O-benzyl tertiary hydroxylamines. (C) 2000 Elsevier Science Ltd.