5692-29-5

Upstream product

• 93-99-2 benzoic acid phenyl ester 
• 462-94-2 1,5-diaminopentane 
• 7647-01-0 hydrogenchloride 
• 84636-44-2 N-benzoyl-ε-aminocapramide 
• 98-88-4 benzoyl chloride 
• 956-09-2 6-(benzoylamino)hexanoic acid 
• 93-58-3 benzoic acid methyl ester 
• 55-21-0 benzamide 
• 93432-24-7 N-(5-iodo-pentyl)-benzamide 
• 74098-30-9 N-(5-chloropentyl)benzamide 
• 92789-03-2 N-(5-nitro-pentyl)-benzamide 

Downstream Products

• 401810-00-2 6-(5-benzoylamino-pentylcarbamoyl)-1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester 
• 313350-04-8 N₁-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide 
• 1276653-40-7 C₁₄H₁₉BrN₂O₂ 
• 462-94-2 1,5-diaminopentane 

Relevant academic research and scientific papers

Chemoselective reductive nucleophilic addition to tertiary amides, secondary amides, and N-methoxyamides

As the complexity of targeted molecules increases in modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide car-bonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor elec-trophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nu-cleophiles to tertiary amides, secondary amides, and N-methoxyamides that uses the Schwartz reagent [Cp2ZrHCl]. The reaction took place in a highly chemoselective fashion in the presence of a variety of sensitive functional groups, such as methyl esters, which conventionally require protection prior to nucleophilic addition. The reaction will be applicable to the concise synthesis of complex natural alkaloids from readily available amide groups.

Improved reagents for newborn screening of mucopolysaccharidosis types I, II, and VI by tandem mass spectrometry

Tandem mass spectrometry for the multiplex and quantitative analysis of enzyme activities in dried blood spots on newborn screening cards has emerged as a powerful technique for early assessment of lysosomal storage diseases. Here we report the design and process-scale synthesis of substrates for the enzymes α-l-iduronidase, iduronate-2-sulfatase, and N-acetylgalactosamine-4- sulfatase that are used for newborn screening of mucopolysaccharidosis types I, II, and VI. The products contain a bisamide unit that is hypothesized to readily protonate in the gas phase, which improves detection sensitivity by tandem mass spectrometry. The products contain a benzoyl group, which provides a useful site for inexpensive deuteration, thus facilitating the preparation of internal standards for the accurate quantification of enzymatic products. Finally, the reagents are designed with ease of synthesis in mind, thus permitting scale-up preparation to support worldwide newborn screening of lysosomal storage diseases. The new reagents provide the most sensitive assay for the three lysosomal enzymes reported to date as shown by their performance in reactions using dried blood spots as the enzyme source. Also, the ratio of assay signal to that measured in the absence of blood (background) is superior to all previously reported mucopolysaccharidosis types I, II, and VI assays.

New Potent Bisubstrate Inhibitors of Histone Acetyltransferase p300: Design, Synthesis and Biological Evaluation

Bisubstrate-type compound Lys-CoA has been shown to inhibit the p300 histone acetyl transferase activity efficiently and may constitute a lead compound for a novel class of anticancer therapeutics. Based on this strategy, we synthesized a series of CoA derivatives and evaluated these molecules for their activity as p300 histone acetyltransferases inhibitor. The best activity was obtained with compound 3 bearing a C-5 spacing linker that connects the CoA moiety to a tert-butyloxycarbonyl (Boc) group. Based on docking simulations, this inhibitor exhibits favorable interactions with two binding areas, namely pockets P1 and P2, within the active site.

Cucurbituril-mediated supramolecular acid catalysis

The rates of acid hydrolysis of N-benzoyl-cadaverine (1), mono-N-(tert-butoxy)carbonyl cadaverine (2), and benzaldoxime (3) with binding motifs for cucurbit[6]uril (1,2) and cucurbit[7]uril (1,3) were investigated in the absence and presence of these hosts. Significant rate enhancements (up to a factor of ca. 300 for the hydrolysis of 3) were observed. Competitive inhibition due to encapsulation of added cadaverine and the successful use of sub-stoichiometric amounts of macrocycle confirmed the function of cucurbiturils in promoting acid hydrolysis.

Amide substituted imidazoquinolines

Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain amide functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.

Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron

(Equation presented) Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.

Amide substituted imidazoquinolines

Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain amide functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.

KINETICS AND MECHANISM OF ACID HYDROLYSIS OF N-BENZOYL-L-LYSINES

Minor differences in acid hydrolysis rates of α- and ε-amide bonds in corresponding N-benzoyl-L-lysines have been found.The reaction is accelerated in the presence of free carboxyl group in the lysine-derivative molecule.The acid dissociation constants KAH of N - and Nε-benzoyl-L-lysines have been determined.Also the substituent effect in benzoyl group on the reaction rate has been examined.A mechanism of the acid hydrolysis of acyl derivatives of lysine is proposed.