Day: November 21, 2022

Taylor, Doris Mia published the artcileIdentifying Oxacillinase-48 Carbapenemase Inhibitors Using DNA-Encoded Chemical Libraries, Application In Synthesis of 39546-32-2, the publication is ACS Infectious Diseases (2020), 6(5), 1214-1227, database is CAplus and MEDLINE.

Bacterial resistance to β-lactam antibiotics is largely mediated by β-lactamases, which catalyze the hydrolysis of these drugs and continue to emerge in response to antibiotic use. β-Lactamases that hydrolyze the last resort carbapenem class of β-lactam antibiotics (carbapenemases) are a growing global health threat. Inhibitors have been developed to prevent β-lactamase-mediated hydrolysis and restore the efficacy of these antibiotics. However, there are few inhibitors available for problematic carbapenemases such as oxacillinase-48 (OXA-48). A DNA-encoded chem. library approach was used to rapidly screen for compounds that bind and potentially inhibit OXA-48. Using this approach, a hit compound, CDD-97(), was identified with submicromolar potency (K_i = 0.53 ± 0.08μM) against OXA-48. X-ray crystallog. showed that CDD-97 binds noncovalently in the active site of OXA-48. Synthesis and testing of derivatives of CDD-97 revealed structure-activity relationships and informed the design of a compound with a 2-fold increase in potency. CDD-97, however, synergizes poorly with β-lactam antibiotics to inhibit the growth of bacteria expressing OXA-48 due to poor accumulation into E. coli. Despite the low in vivo activity, CDD-97 provides new insights into OXA-48 inhibition and demonstrates the potential of using DNA-encoded chem. technol. to rapidly identify β-lactamase binders and to study β-lactamase inhibition, leading to clin. useful inhibitors.

ACS Infectious Diseases published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C15H25BN2O4, Application In Synthesis of 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Vettorazzi, Marcela published the artcileAn integrative study to identify novel scaffolds for sphingosine kinase 1 inhibitors, Quality Control of 39546-32-2, the publication is European Journal of Medicinal Chemistry (2017), 461-481, database is CAplus and MEDLINE.

Sphingosine kinase 1 (SphK1), the enzyme that produces the bioactive sphingolipid metabolite, sphingosine-1-phosphate, is a promising new mol. target for therapeutic intervention in cancer and inflammatory diseases. In view of its importance, the main objective of this work was to find new and more potent inhibitors for this enzyme possessing different structural scaffolds than those of the known inhibitors. The authors’ theor. and exptl. study has allowed the authors to identify two new structural scaffolds (three new compounds), which could be used as starting structures for the design and then the development of new inhibitors of SphK1. The authors’ study was carried out in different steps: virtual screening, synthesis, bioassays and mol. modeling. From the results, the authors propose a new dihydrobenzo[b]pyrimido[5,4-f]azepine and two alkyl{3-/4-[1-hydroxy-2-(4-arylpiperazin-1-yl)ethyl]phenyl}carbamates as initial structures for the development of new inhibitors. In addition, the authors’ mol. modeling study using QTAIM calculations, allowed the authors to describe in detail the mol. interactions that stabilize the different Ligand-Receptor complexes. Such analyses indicate that the cationic head of the different compounds must be refined to obtain an increase in the binding affinity of these ligands.

European Journal of Medicinal Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C8H11NO, Quality Control of 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Maricich, Tom J. published the artcileReaction of benzenesulfinyl azide with thiols and amines. Preparation of thiosulfinates and sulfinamides, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (1984), 49(11), 1931-4, database is CAplus.

Treating PhS(O)N₃ with RSH (R = Ph, PhCH₂, Pr, Me₂CH, Me₃C, HOCH₂CH₂, Me₃CCH₂) at -20° gave PhS(O)SR and HN₃. A similar reaction using R¹NHR² [R¹ = Ph, Bu, HOCH₂CH₂, R² = H; R¹R² = (CH₂)₅] gave PhS(O)NR¹R² and HN₃. Thiosulfinates and sulfinamides containing a free OH group could be prepared Yields ranged from 41 to 93%.

Journal of Organic Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Fries, David S. published the artcileSynthesis and preliminary pharmacological activity of aminoalkoxy isosteres of glycolate ester anticholinergics, SDS of cas: 13444-24-1, the publication is Journal of Medicinal Chemistry (1977), 20(10), 1250-4, database is CAplus and MEDLINE.

Five 2-[(dialkylamino)alkoxy]-1,1-diphenylethanols and 5 2-(N-heterocycleoxy)-1,1-diphenylethanols were prepared by the reaction of 2,2-diphenyloxirane [882-59-7] with the alkoxide form of the appropriate amino alc. Most of the compounds had moderate anticholinergic activity when tested on the isolated rat jejunum or for inhibition of perphenazine-induced catatonia in rats. The most active compounds were I [63624-24-8], II [63624-25-9], and III [63624-26-0]. Structure-activity relations are discussed.

Journal of Medicinal Chemistry published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, SDS of cas: 13444-24-1.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Meador, Rowan I. L. published the artcileTandem elimination-oxidation of tertiary benzylic alcohols with an oxoammonium salt, COA of Formula: C11H21BF4N2O2, the publication is Organic & Biomolecular Chemistry (2021), 19(28), 6233-6236, database is CAplus and MEDLINE.

Tertiary benzylic alcs. reacted with oxoammonium salts, underwent a tandem elimination/allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provided a rapid entry into allylic ethers from certain benzylic tertiary alcs. The allylic ether cleaved under reductive conditions to reveal the allylic alc.

Organic & Biomolecular Chemistry published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, COA of Formula: C11H21BF4N2O2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Johnson, Henry W. B. published the artcileDiscovery of Highly Selective Inhibitors of the Immunoproteasome Low Molecular Mass Polypeptide 2 (LMP2) Subunit, HPLC of Formula: 72002-30-3, the publication is ACS Medicinal Chemistry Letters (2017), 8(4), 413-417, database is CAplus and MEDLINE.

Building upon the success of bortezomib (VELCADE) and carfilzomib (KYPROLIS), the design of a next generation of inhibitors targeting specific subunits within the immunoproteasome is of interest for the treatment of autoimmune disease. There are three catalytic subunits within the immunoproteasome (low mol. mass polypeptide-7, -2, and multicatalytic endopeptidase complex subunit-1; LMP7, LMP2, and MECL-1), and a campaign was undertaken to design a potent and selective LMP2 inhibitor with sufficient properties to allow for sustained inhibition in vivo. Screening a focused library of epoxyketones revealed a series of potent dipeptides that were optimized to provide the highly selective inhibitor KZR-504 (12).

ACS Medicinal Chemistry Letters published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C6H9NO3, HPLC of Formula: 72002-30-3.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Down, Kenneth published the artcileDiscovery of GSK251: A Highly Potent, Highly Selective, Orally Bioavailable Inhibitor of PI3Kδ with a Novel Binding Mode, SDS of cas: 859833-21-9, the publication is Journal of Medicinal Chemistry (2021), 64(18), 13780-13792, database is CAplus and MEDLINE.

Optimization of a previously reported lead series of PI3Kδ inhibitors with a novel binding mode led to the identification of a clin. candidate compound 31 (GSK251)(I). Removal of an embedded Ames-pos. heteroaromatic amine by reversing a sulfonamide followed by locating an interaction with Trp760 led to a highly selective compound 9 (II). Further optimization to avoid glutathione trapping, to enhance potency and selectivity, and to optimize an oral pharmacokinetic profile led to the discovery of compound 31 (GSK251) that had a low predicted daily dose (45 mg, b.i.d) and a rat toxicity profile suitable for further development.

Journal of Medicinal Chemistry published new progress about 859833-21-9. 859833-21-9 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Boronic Acids,Boronate Esters, name is 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, and the molecular formula is C18H28BNO2, SDS of cas: 859833-21-9.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Waser, Philipp published the artcileAn RCM-Based Total Synthesis of the Antibiotic Disciformycin B, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Angewandte Chemie, International Edition (2020), 59(40), 17393-17397, database is CAplus and MEDLINE.

The total synthesis of the potent new antibiotic disciformycin B is described, which shows significant activity against methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA/VRSA) strains. The synthetic route is based on macrocyclization of a tetraene substrate to the 12-membered macrolactone core by ring-closing olefin metathesis (RCM). Although macrocyclization was accompanied by concomitant cyclopentene formation by an alternative RCM pathway, conditions were established to give the macrocycle as the major product. Key steps in the construction of the Ring Closure Metathesis substrate include a highly efficient Evans syn-aldol reaction, the asym. Brown allylation of angelic aldehyde, and the stereoselective Zn(BH₄)₂-mediated 1,2-reduction of an enone. The synthesis was completed by late-stage dehydrative glycosylation to introduce the D-arabinofuranosyl moiety and final chemoselective allylic alc. oxidation

Angewandte Chemie, International Edition published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C15H21BO3, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Rizwan, Muhammad published the artcileSynthesis, characterization, HOMO-LUMO study, and antimicrobial activity of organotin(IV) complexes of 4-piperidine carboxamide and its Schiff base, HPLC of Formula: 39546-32-2, the publication is Journal of Coordination Chemistry (2014), 67(2), 341-351, database is CAplus.

A series of organotin(IV) complexes has been synthesized by reacting 4-piperidine carboxamide with CS₂ and R₂SnCl₂/R₃SnCl in 1 : 1 M/L ratio at room temperature The synthesized complexes were further treated with benzaldehyde to synthesize Schiff bases under stirring. All the complexes were characterized by elemental anal., FT-IR, ¹H and ¹³C NMR. FT-IR and semi-empirical study confirm the bidentate nature of ligand. The complexes exhibit four-coordinate geometry in solution Thermodn. parameters and mol. descriptors were calculated by using semi-empirical PM3 method. HOMO-LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack when compared with triorganotin complexes. Neg. heats of formation at 298 K demonstrate that , and are thermodynamically stable. The antimicrobial results have shown that complexes containing Schiff base exhibit significantly better activity compared to complexes with carboxamide derivatives

Journal of Coordination Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, HPLC of Formula: 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Hammer, C. F. published the artcileReactions of β-substituted amines. III. Complete product study of the reactions of 3-chloro-1-ethylpiperidine and 2-(chloromethyl)-1-ethylpyrrolidine with hydroxide ion, Application of 1-Ethylpiperidin-3-ol, the publication is Tetrahedron (1973), 29(13), 1767-72, database is CAplus.

3-Chloro-1-ethylpiperidine (I) in 10% NaOH gave 1-ethyl-2-(hydroxymethyl)pyrrolidine 22, 1-ethyl-3-hydroxypiperidine 42, 2,2′-bis(N-ethyl-2-pyrrolidinomethyl) ether 16, 3-(N-ethyl-2-pyrrolidinylmethoxy)-N-ethylpiperidine 16, and 3,3′-bis(N-ethyl-3-piperidinyl) ether 2%. The products were separated by gas liquid chromatog. The MeOH solvate of 2-(chloromethyl)-1-ethylpyrrolidine hydrochloride in 25% NaOH gave the same products and 1-ethyl-2-(methoxymethyl)pyrrolidine and 1-ethyl-3-methoxypiperidine. The reaction of I with EtO- was also examined

Tetrahedron published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Application of 1-Ethylpiperidin-3-ol.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem