Category: 53636-56-9

Cheng, Xiayun; Taylor, Alexandria P.; Zhu, Kaicheng published the artcile< Synthesis of Substituted 2-Pyridones via 6π-Electrocyclization of Dienyl Isocyanates>, Name: Methyl 3-bromo-2-pyridinecarboxylate, the main research area is substituted pyridone preparation; dienyl isocyanate pi electrocyclization Curtius.

A one-pot Curtius rearrangement of dienyl carboxylic acids followed by a 6π-electrocyclization process to form substituted 2-pyridone products was developed. Dienyl isocyanates generated from aliphatic acids were more reactive than their aromatic counterparts. Addnl., substitution patterns of the carboxylic acids had an impact on the efficiency of the cyclization.

Journal of Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Name: Methyl 3-bromo-2-pyridinecarboxylate.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pierre, Fabrice; Chua, Peter C.; O’Brien, Sean E.; Siddiqui-Jain, Adam; Bourbon, Pauline; Haddach, Mustapha; Michaux, Jerome; Nagasawa, Johnny; Schwaebe, Michael K.; Stefan, Eric; Vialettes, Anne; Whitten, Jeffrey P.; Chen, Ta Kung; Darjania, Levan; Stansfield, Ryan; Anderes, Kenna; Bliesath, Josh; Drygin, Denis; Ho, Caroline; Omori, May; Proffitt, Chris; Streiner, Nicole; Trent, Katy; Rice, William G.; Ryckman, David M. published the artcile< Discovery and SAR of 5-(3-Chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylic Acid (CX-4945), the first clinical stage inhibitor of protein kinase CK2 for the treatment of cancer>, Reference of 53636-56-9, the main research area is naphthyridinecarboxylic acid derivative CX4945 preparation antitumor structure activity; protein kinase CK2 target antitumor CX 4945 preparation.

Herein we chronicle the discovery of CX-4945 (I), a first-in-class, orally bioavailable ATP-competitive inhibitor of protein kinase CK2 in clin. trials for cancer. CK2 has long been considered a prime cancer drug target because of the roles of deregulated and overexpressed CK2 in cancer-promoting pro-survival and antiapoptotic pathways. These biol. properties as well as the suitability of CK2’s small ATP binding site for the design of selective inhibitors, led us to fashion novel therapeutic agents for cancer. The optimization leading to I (Ki = 0.38 nM) was guided by mol. modeling, suggesting a strong binding of I resulting from a combination of hydrophobic interactions, an ionic bridge with Lys68, and hydrogen bonding with the hinge region. I was highly selective, orally bioavailable across species (20-51%) and efficacious in xenograft models. The discovery of I will allow the therapeutic targeting of CK2 in humans for the first time.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Reference of 53636-56-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Sahani, Rajkumar Lalji; Diana-Rivero, Raquel; Vernekar, Sanjeev Kumar V.; Wang, Lei; Du, Haijuan; Zhang, Huanchun; Castaner, Andres Emanuelli; Casey, Mary C.; Kirby, Karen A.; Tedbury, Philip R.; Xie, Jiashu; Sarafianos, Stefan G.; Wang, Zhengqiang published the artcile< Design, synthesis and characterization of HIV-1 CA-targeting small molecules: conformational restriction of PF74>, Computed Properties of 53636-56-9, the main research area is indolyl pyridyl amide preparation antiviral SAR cytotoxicity mol docking; imidazolyl indolyl amide preparation antiviral SAR cytotoxicity mol docking; HIV-1; PF74; capsid protein; conformational constraint; metabolic stability.

Designed and synthesized three series of PF74-like analogs featuring conformational constraints at the aniline terminus or the phenylalanine carboxamide moiety, and characterized them using a biophys. thermal shift assay (TSA), cell-based antiviral and cytotoxicity assays, and in vitro metabolic stability assays in human and mouse liver microsomes. These studies showed that the two series with the phenylalanine carboxamide moiety replaced by a pyridine or imidazole ring can provide viable hits. Subsequent SAR identified an improved analog I which effectively inhibited HIV-1 (EC50 = 0.31μM), strongly stabilized CA hexamer (ΔTm = 8.7°C), and exhibited substantially enhanced metabolic stability (t1/2 = 27 min for 15 vs. 0.7 min for PF74). Metabolic profiles from the microsomal stability assay also indicate that blocking the C5 position of the indole ring could lead to increased resistance to oxidative metabolism

Viruses published new progress about Amides Role: PAC (Pharmacological Activity), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Computed Properties of 53636-56-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Conde, Nerea; SanMartin, Raul; Herrero, Maria Teresa; Dominguez, Esther published the artcile< Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids>, Product Details of C7H6BrNO2, the main research area is alkynoic acid cycloisomerization palladium NNC pincer complex catalyst.

A two-step (nucleophilic substitution/palladation by oxidative addition) sequence provides a high-yielding access to a non-sym. palladium NNC pincer complex. A number of terminal and internal alkynoic acids with different substitution patterns at the α- and β-positions are regio- and diastereoselectively cycloisomerized to the corresponding exocyclic enol lactones in the presence of exceedingly low amounts of the latter palladium complex, so that unprecedented turnover numbers and frequencies ranging from 1000,000 to 700,000 and from 41,667 to 9722 h-1, resp., are achieved. The optimized protocol, based on the use of a catalytic amount of triethylamine as base, allows an easy real-time monitoring of the reaction by NMR spectroscopy. Several pieces of evidence in favor of the direct participation of the above pincer complex as the catalyst of the reaction were gathered from kinetic and poisoning experiments

Advanced Synthesis & Catalysis published new progress about Carboxylic acids, alkynyl Role: RCT (Reactant), RACT (Reactant or Reagent). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Product Details of C7H6BrNO2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Stauffer, Kenneth J.; Williams, Peter D.; Selnick, Harold G.; Nantermet, Philippe G.; Newton, Christina L.; Homnick, Carl F.; Zrada, Matthew M.; Lewis, S. Dale; Lucas, Bobby J.; Krueger, Julie A.; Pietrak, Beth L.; Lyle, Elizabeth A.; Singh, Rominder; Miller-Stein, Cynthia; White, Rebecca B.; Wong, Bradley; Wallace, Audrey A.; Sitko, Gary R.; Cook, Jacquelyn J.; Holahan, Marie A.; Stranieri-Michener, Maria; Leonard, Yvonne M.; Lynch, Joseph J. Jr.; McMasters, Daniel R.; Yan, Youwei published the artcile< 9-Hydroxyazafluorenes and Their Use in Thrombin Inhibitors>, Category: pyridine-derivatives, the main research area is hydroxyazafluorene derivative preparation thrombin inhibitor anticoagulant thrombosis crystal structure.

Optimization of a previously reported thrombin inhibitor, 9-hydroxy-9-fluorenylcarbonyl-L-prolyl-trans-4-aminocyclohexylmethylamide (1), by replacing the aminocyclohexyl P1 group provided a new lead structure, 9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-aminomethyl-5-chlorobenzylamide (2), with improved potency (Ki = 0.49 nM for human thrombin, 2× APTT = 0.37 μM in human plasma) and pharmacokinetic properties (F = 39%, iv T1/2 = 13 h in dogs). An effective strategy for reducing plasma protein binding of 2 and improving efficacy in an in vivo thrombosis model in rats was to replace the lipophilic fluorenyl group in P3 with an azafluorenyl group. Systematic investigation of all possible azafluorenyl P3 isomers and azafluorenyl-N-oxide analogs of 2 led to the identification of an optimal compound, 3-aza-9-hydroxyfluoren-9(R)-ylcarbonyl-L-prolyl-2-aminomethyl-5-chlorobenzylamide (I), with high potency (Ki = 0.40 nM, 2× APTT = 0.18 μM), excellent pharmacokinetic properties (F = 55%, T1/2 = 14 h in dogs), and complete efficacy in the in vivo thrombosis model in rats (inhibition of FeCl3-induced vessel occlusions in six of six rats receiving an i.v. infusion of 10 μg/kg/min of I). The stereochem. of the azafluorenyl group in I was determined by x-ray crystallog. anal. of its N-oxide derivative bound in the active site of human thrombin.

Journal of Medicinal Chemistry published new progress about Anticoagulants. 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Dziuganowska, Zofia A.; Slepokura, Katarzyna; Volle, Jean-Noel; Virieux, David; Pirat, Jean-Luc; Kafarski, Pawel published the artcile< Structural Analogues of Selfotel>, Recommanded Product: Methyl 3-bromo-2-pyridinecarboxylate, the main research area is phosphonate pyridinecarboxylic piperidinecarboxylic preparation phosphonylation bromopyridine hydrogenation; NMDA antagonist library phosphonate pyridinecarboxylic piperidinecarboxylic acid preparation activity; crystal structure phosphonate pyridinecarboxylic piperidinecarboxylic acid NMDA antagonist; mol structure phosphonate pyridinecarboxylic piperidinecarboxylic acid NMDA antagonist.

A small library of phosphonopiperidylcarboxylic acids, analogs of NMDA antagonist selfotel (CGS 19755), was synthesized. First, the series of aromatic esters was obtained via a palladium-catalyzed cross-coupling reaction (Hirao coupling) of dialkyl phosphites with bromopyridinecarboxylates, followed by their hydrolysis. Then, hydrogenation of the resulting phosphonopyridylcarboxylic acids over PtO2 yielded the desired phosphonopiperidylcarboxylic acids. NMR studies indicated that the hydrogenation reaction proceeds predominantly by cis addition Several compounds were obtained as monocrystal structures. Preliminary biol. studies performed on cultures of neurons suggest that the obtained compounds possess promising activity toward NMDA receptors.

Journal of Organic Chemistry published new progress about Carboxylic esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Recommanded Product: Methyl 3-bromo-2-pyridinecarboxylate.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kuwata, Yoshiyuki; Sonoda, Motohiro; Tanimori, Shinji published the artcile< Facile Synthesis of Phenanthridinone Alkaloids via Suzuki-Miyaura Cross-coupling>, Electric Literature of 53636-56-9, the main research area is phenanthridinone alkaloid crinasiadine dihydrobicolorine trisphaeridine bicolorine facile synthesis; aminophenylboronic acid Suzuki Miyaura cross coupling bromobenzoate bromoheteroarenecarboxylate.

Phenanthridinone alkaloids crinasiadine (I) and N-alkylcrinasiadines II [R = CH2CH2CHMe2, CH2CH2CO2Et, CH2CH2Ph, CH2CH2CH2CO2Et] have been synthesized based on palladium-catalyzed tandem C-C and C-N bond formation starting from 2-aminophenylboronic acid and 2-bromobenzoate in short steps. Related alkaloids, 5,6-dihydrobicolorine (III), trisphaeridine (IV), and bicolorine (V) have also been synthesized.

Journal of Heterocyclic Chemistry published new progress about Alkaloids Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (phenanthridine). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Electric Literature of 53636-56-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Sanders, Georgine M.; Van Dijk, M.; Van der Plas, H. C. published the artcile< Reactions of haloquinolizinium bromides with diethylamine>, Recommanded Product: Methyl 3-bromo-2-pyridinecarboxylate, the main research area is quinolizinium bromide diethylamine reaction.

The reactions of quinolizinium bromide (QB) and its four monobromo derivatives with diethylamine have been investigated. For Br in position 2 or 4, substitution is the main process, whereas for Br in positions 1 and 3 quant. ring opening is found. The substituted pyridylbutadienes formed by ring opening, are cis-trans-butadienes, which isomerize into the all-trans forms. The steric course of the ring opening is explained.

Journal of Heterocyclic Chemistry published new progress about 53636-56-9. 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Recommanded Product: Methyl 3-bromo-2-pyridinecarboxylate.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Dunn, A. D. published the artcile< The addition of hydroxylamine to derivatives of halopyridine carboxylic acids>, Recommanded Product: Methyl 3-bromo-2-pyridinecarboxylate, the main research area is halopyridinecarboxylate hydroxylamine addition; pyridinecarboxylate halo hydroxylamine addition; halopyridinenitrile hydroxylamine cyclization; isoxazolopyridine.

Cyanopyridines I (R = Cl, R1 = cyano, R2 = H; R = cyano, R1 = Cl, R2 = H; R = H, R1 = cyano, R2 = Cl) reacted with a MeOH solution of NH2OH and MeONa to give isoxazolopyridines. Thus, I (R = Cl, R1 = cyano, R2 = H) gave isoxazolopyridine II. However, I (R = H, R1 = Cl, R2 = cyano) reacted with the same reagent to give I (R, R1, same, R2 = CONH2), and I (R = H, R1 = Br, R2 = cyano) gave I [R, R1, same, R2 = C(:NOH)NH2]. No bicyclic products were formed . Esters I (R = Cl, R1 = CO2Me, R2 = H) reacted with the same reagent to give the hydroxamic acids I (R, R2, same, R1 = CONHOH). Similarly esters I (R = CO2Me, R1 = Br, R2 = H; R= H, R1 = Br, R2 = CO2Me) also gave the corresponding hydroxamic acids.

Zeitschrift fuer Chemie published new progress about Cyclocondensation reaction. 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Recommanded Product: Methyl 3-bromo-2-pyridinecarboxylate.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Mancuso, Raffaella; Novello, Mariangela; Russo, Patrizio; Palumbo Piccionello, Antonio; Gabriele, Bartolo published the artcile< Iodolactonization of 3-Alkynylthiophene-2-Carboxylic and 3-Alkynylpicolinic Acids for the Synthesis of Fused Heterocycles>, Name: Methyl 3-bromo-2-pyridinecarboxylate, the main research area is fused heterocycle preparation iodolactonization alkynylthiophenecarboxylate alkynylpicolinate.

The iodolactonization of 3-alkynylthiophene-2-carboxylic acids and 3-alkynylpicolinic acids was studied. Using I2 as the iodine source and NaHCO3 as the base in MeCN, the process took place smoothly to afford thienopyranones and pyranopyridinones, resp., from 6-endo-dig cyclization. The method also worked nicely for the transformation of 2-(phenylethynyl)thiophene-3-carboxylic acid and 3-(phenylethynyl)isonicotinic acid into 7-iodo-6-phenyl-4H-thieno[3,2-c]pyran-4-one and 4-iodo-3-phenyl-1H-pyrano[4,3-c]pyridin-1-one, resp. Although with some 3-alkynylpicolinic acids the process led to a mixture of the 6-endo-dig and 5-exo-dig products, it could be still made selective toward the pyranopyridinone compound working in 1-ethyl-3-methylimidazolium Et sulfate as the solvent. However, the exclusive formation of the 5-exo-dig product was observed in N-ethyl-N-methylmorpholinium dicyanamide starting from 3-(3,3-dimethylbut-1-yn-1-yl)picolinic acid. Some representative iodinated thienopyridinone products were successfully used as substrates for Pd-catalyzed Suzuki and Sonogashira reactions.

European Journal of Organic Chemistry published new progress about Carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (3-Alkynylthiophene-2-Carboxylic Acids). 53636-56-9 belongs to class pyridine-derivatives, and the molecular formula is C7H6BrNO2, Name: Methyl 3-bromo-2-pyridinecarboxylate.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem