Month: October 2022

Reference of 6-Bromopyridin-3-amineIn 2020 ,《Synthesis of novel hybrid quinolino[4,3-b][1,5]naphthyridines and quinolino[4,3-b][1,5]naphthyridin-6(5H)-one derivatives and biological evaluation as topoisomerase I inhibitors and antiproliferatives》 appeared in European Journal of Medicinal Chemistry. The author of the article were Martin-Encinas, Endika; Selas, Asier; Tesauro, Cinzia; Rubiales, Gloria; Knudsen, Birgitta R.; Palacios, Francisco; Alonso, Concepcion. The article conveys some information:

The topoisomerase I enzymic inhibition of hybrid quinolino [4,3-b][1,5]naphthyridines I [R1 = H, 9-OMe, 9-Br, 11-Br; R2 = H, tosyl; X = CH2, CO] and quinolino [4,3-b][1,5]naphthyridin-6(5H)-ones II [R3 = H, 9-OMe, 9-Br, 11-Br; X = CH2, CO] were investigated. First, the synthesis of these fused compounds was performed by intramol. [4 + 2]-cycloaddition reaction of functionalized aldimines obtained by the condensation of 3-aminopyridine and unsaturated aldehydes afforded corresponding hybrid 5-tosylhexahydroquinolino [4,3-b][1,5]naphthyridines I [R2 = tosyl; X = CH2] tetrahydroquinolino [4,3-b][1,5]naphthyridin-6(5H)-one compound I [R2 = tosyl; X = CO] with good to high yields. Subsequent dehydrogenation led to the corresponding more unsaturated dihydro [1,5]naphthyridine II [X = CH2] and [1,5]naphthyridin-6(5H)-one derivs II [X = CO] in quant. yields. Deprotection of tosyl group in compounds I [R1 = H, 9-Br; R2 = tosyl; X = CH2] with magnesium in acidic conditions led to hexahydroquinolino[4,3-b][1,5]naphthyridines derivatives I [R1 = H, 9-Br; R2 = H; X = CH2]. The new polycyclic products compounds I and II showed excellent-good activity as topoisomerase I (TopI) inhibitors that lead to TopI induced nicking of plasmids. This was consistent with the compounds acted as TopI poisons resulting in the accumulation of trapped cleavage complexes in the DNA. The cytotoxic effect on cell lines A549, SKOV3 and on non-cancerous MRC5 was also screened. Compound I [R1 = H; R2 = tosyl; X = CO] resulted the most cytotoxic compound with IC50 values of 3.25 ± 0.91μM and 2.08 ± 1.89μM against the A549 cell line and the SKOV3 cell line, resp. Also, compounds I [R1 = H; R2 = tosyl; X = CH2] and II [R3 = H] showed good cytotoxicity against these cell lines. None of the compounds presented cytotoxic effects against non-malignant pulmonary fibroblasts (MRC-5).6-Bromopyridin-3-amine(cas: 13534-97-9Reference of 6-Bromopyridin-3-amine) was used in this study.

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Reference of 6-Bromopyridin-3-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C7H7NOIn 2022 ,《(Electro)chemical and antimicrobial characterization of novel Ru(II) bipyridine complexes with acetylpyridine analogs》 was published in Journal of Coordination Chemistry. The article was written by Mihajlovic-Lalic, Ljiljana E.; Stankovic, Dalibor; Novakovic, Irena; Grguric-Sipka, Sanja. The article contains the following contents:

Three ruthenium-bipyridine complexes (1-3) carrying acetylpyridine ligand unit were synthesized in methanol via the reaction of [RuCl2(bpy)2] with corresponding acetylpyridine (2-, 3-, and 4-acpy). Obtained complexes were characterized by (1H and 13C) NMR and IR spectroscopy, MS spectrometry, UV-visible spectrophotometry, and cyclic voltammetry. Their structural characterization revealed bidentate coordination mode for 2-acpy while 3- and 4-acpy acted as monodentate ligands. The electrochem. profile of newly synthesized compounds was studied by cyclic voltammetry which confirmed their electrochem. activity. Voltammetric responses within the -1.20 < Ep < 1.50 v range of potentials were summarized in two major events: Ru(II)→Ru(III) oxidation spotted at apparatus ΔEp = 0.65 v and successive reductions of bpy units located from -0.79 v to 0.47 v (vs. Ag/AgCl (3 M) electrode). The DNA-binding activity of the complexes was evaluated by both UV-visible spectrophotometry and cyclic voltammetry indicating DNA-intercalation with a slight contribution of electrostatic interactions. Furthermore, antimicrobial activity was tested against bacterial and fungal strains, for which moderate activity was observed Assessment of in vitro toxicity against freshly hatched nauplii of Artemia salina as well as radical scavenging capacity was evaluated. The test compounds showed neither toxicity nor antioxidant activity. The results came from multiple reactions, including the reaction of 4-Acetylpyridine(cas: 1122-54-9Synthetic Route of C7H7NO)

4-Acetylpyridine(cas: 1122-54-9) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Synthetic Route of C7H7NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of Picolinic acidIn 2019 ,《Structure and mechanism of piperideine-6-carboxylate dehydrogenase from Streptomyces clavuligerus》 was published in Acta Crystallographica, Section D: Structural Biology. The article was written by Hasse, Dirk; Hulsemann, Janne; Carlsson, Gunilla H.; Valegaard, Karin; Andersson, Inger. The article contains the following contents:

The core of β-lactam antibiotics originates from amino acids of primary metabolism in certain microorganisms. β-Lactam-producing bacteria, including Streptomyces clavuligerus, synthesize the precursor of the amino acid α-aminoadipic acid by the catabolism of lysine in two steps. The second reaction, the oxidation of piperideine-6-carboxylate (or its open-chain form α-aminoadipate semialdehyde) to α-aminoadipic acid, is catalyzed by the NAD+-dependent enzyme piperideine-6-carboxylate dehydrogenase (P6CDH). This structural study, focused on ligand binding and catalysis, presents structures of P6CDH from S. clavuligerus in its apo form and in complexes with the cofactor NAD+, the product α-aminoadipic acid and a substrate analog, picolinic acid. P6CDH adopts the common aldehyde dehydrogenase fold, consisting of NAD-binding, catalytic and oligomerization domains. The product binds in the oxyanion hole, close to the catalytic residue Cys299. Clear d. is observed for the entire cofactor, including the nicotinamide riboside, in the binary complex. NAD+ binds in an extended conformation with its nicotinamide ring overlapping with the binding site of the carboxylate group of the product, implying that the conformation of the cofactor may change during catalysis. The binding site of the substrate analog overlaps with that of the product, suggesting that the cyclic form of the substrate, piperideine-6-carboxylate, may be accepted as a substrate by the enzyme. The catalytic mechanism and the roles of individual residues are discussed in light of these results. In the experiment, the researchers used Picolinic acid(cas: 98-98-6Reference of Picolinic acid)

Picolinic acid(cas: 98-98-6) is used as a chelate for alkaline earth metals. Used to prepare picolinato ligated transition metal complexes. In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.Reference of Picolinic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Mou, Xue-Qing; Chen, Xiang-Yu; Chen, Gong; He, Gang published 《Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates: facile synthesis of 1,2-amino alcohols》.Chemical Communications (Cambridge, United Kingdom) published the findings.Product Details of 103-74-2 The information in the text is summarized as follows:

A new radical-mediated intramol. β-C(sp3)-H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alc. starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcs. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)-H functionalization of alcs. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative. In the experimental materials used by the author, we found 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Product Details of 103-74-2)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Product Details of 103-74-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Sattigeri, Jitendra A.; Garg, Malvika; Bhateja, Pragya; Soni, Ajay; Rauf, Abdul Rehman Abdul; Gupta, Mahendrakumar; Deshmukh, Mahesh S.; Jain, Tarun; Alekar, Nidhi; Barman, Tarani Kanta; Jha, Paras; Chaira, Tridib; Bambal, Ramesh B.; Upadhyay, Dilip J.; Nishi, Takahide published 《Synthesis and evaluation of thiomannosides, potent and orally active FimH inhibitors》.Bioorganic & Medicinal Chemistry Letters published the findings.Application In Synthesis of 5-Bromo-2-chloropyridine The information in the text is summarized as follows:

FimH is a type I fimbrial lectin located at the tip of type-1 pili of Gram-neg. uropathogenic Escherichia coli (UPEC) guiding its ability to adhere and infect urothelial cells. Accordingly, blocking FimH with small mol. inhibitor is considered as a promising new therapeutic alternative to treat urinary tract infections caused by UPEC. Herein, we report that compounds having the S-glycosidic bond (thiomannosides) had improved metabolic stability and plasma exposures when dosed orally. Especially compound 5h showed the potential to inhibit biofilm formation and also to disrupt the preformed biofilm. And compound 5h showed prophylactic effect in UTI model in mice. The experimental process involved the reaction of 5-Bromo-2-chloropyridine(cas: 53939-30-3Application In Synthesis of 5-Bromo-2-chloropyridine)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Application In Synthesis of 5-Bromo-2-chloropyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Applied Organometallic Chemistry included an article by Thimma Sambamoorthy, Manikandan; Rengan, Ramesh; Jan Grzegorz, Malecki. Product Details of 3510-66-5. The article was titled 《Efficient construction of C-C bonds from aryl halides/aryl esters with arylboronic acids catalyzed by palladium(II) thiourea complexes》. The information in the text is summarized as follows:

A new set of palladium(II) complexes comprising phenyl(thiazolyl)thiourea ligands I (R = H, Me, NO2) have been successfully synthesized and characterized with the aid of anal. as well as spectral (IR, UV-visible and NMR) methods. A distorted square-planar geometry with N^S coordination mode of thiourea ligands in the new palladium complexes I (R = H, Me) was corroborated by single-crystal X-ray diffraction methods. Interestingly, the palladium(II) thiourea complexes I showed the highest catalytic activity with 0.1 mol% catalyst loading in Suzuki-Miyaura cross-coupling reactions utilizing a range of aryl halides RX (R = 4-acetylphenyl, 5-methylpyridin-2-yl, pyridin-2-yl, etc.; X = Br, Cl) with arylboronic acids R1B(OH)2 (R1 = Ph, 4-chlorophenyl, 6-bromopyridin-3-yl, etc.) as coupling partners in aqueous-organic media. Syntheses of diaryl ketones PhCOR1 using Ph benzoate and arylboronic acids as coupling partners were also achieved with low catalyst loading within 20 h. The potential of prepared catalyst was demonstrated by its wide substrate scope, low catalyst loadings and high isolated yield. Moreover, the influences of key parameters like solvent, base, temperature and catalyst loading were also investigated. In the experiment, the researchers used 2-Bromo-5-methylpyridine(cas: 3510-66-5Product Details of 3510-66-5)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridine’s structure is isoelectronic with that of benzene, but its properties are quite different. Pyridine is completely miscible with water, whereas benzene is only slightly soluble. Like all hydrocarbons, benzene is neutral (in the acid–base sense), but because of its nitrogen atom, pyridine is a weak base.Product Details of 3510-66-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Chemical Communications (Cambridge, United Kingdom) included an article by Teng, Kun-Xu; Niu, Li-Ya; Li, Jie; Jia, Lu; Yang, Qing-Zheng. Safety of 4-Ethynylpyridine. The article was titled 《An unexpected coupling-reduction tandem reaction for the synthesis of alkenyl-substituted BODIPYs》. The information in the text is summarized as follows:

We report an unexpected coupling-reduction tandem reaction as a general and efficient one-pot synthesis of alkenyl-substituted boron dipyrromethene (BODIPY) from chlorinated-BODIPY and alkyne. This unique synthesis combined the Sonogashira coupling reaction and reduction reaction without adding an addnl. reagent, which shows higher yields, broader substrate scope and faster reaction rate compared with the conventional methods of the Knoevenagel reaction and Heck coupling reaction. In the experiment, the researchers used 4-Ethynylpyridine(cas: 2510-22-7Safety of 4-Ethynylpyridine)

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Safety of 4-Ethynylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Chemical Communications (Cambridge, United Kingdom) included an article by Luo, Xuewei; Fan, Zhengning; Zhang, Bo; Chen, Chao; Xi, Chanjuan. Computed Properties of C33H24IrN3. The article was titled 《Visible-light-triggered direct keto-difluoroacetylation of styrenes with (fluorosulfonyl)difluoroacetate and dimethyl sulfoxide leading to α-difluoroacetylated ketones》. The information in the text is summarized as follows:

Photoredox-catalyzed direct keto-difluoroacetylation of styrenes with (fluorosulfonyl)difluoroacetate and DMSO as an oxidant is disclosed. A variety of α-difluoroacetylated ketones bearing functional groups with good yields are obtained using fac-Ir(ppy)3 as a photocatalyst under visible light irradiation In the experiment, the researchers used many compounds, for example, fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6Computed Properties of C33H24IrN3)

fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Computed Properties of C33H24IrN3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Copper-catalysed three-component carboiodination of arynes: expeditious synthesis of o-alkynyl aryl iodides》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Cao, Wenxuan; Niu, Sheng-Li; Shuai, Li; Xiao, Qing. Related Products of 2510-22-7 The article mentions the following:

A copper-catalyzed three-component iodoalkynylation reaction of arynes for the expeditious and versatile synthesis of o-alkynyl aryl iodides was developed. Mechanism research shows that the reaction goes through two steps enabled by copper catalysis: the formation of 1-iodo-2-arylacetylene and the insertion of the aryne into a C(sp)-I bond.4-Ethynylpyridine(cas: 2510-22-7Related Products of 2510-22-7) was used in this study.

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Related Products of 2510-22-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《A conjugated microporous polymer as a recyclable heterogeneous ligand for highly efficient regioselective hydrosilylation of allenes》 was written by Jiang, Ya-Nan; Zeng, Jia-Hao; Yang, Ying; Liu, Zhi-Kai; Chen, Jun-Jia; Li, Ding-Chang; Chen, Li; Zhan, Zhuang-Ping. Electric Literature of C5H3Br2N And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020. The article conveys some information:

Pyridines containing adjacent CC bonds were utilized as ligand units and integrated into the skeleton of conjugated microporous polymers. The resultant Pd-CMP-1 was first applied as a highly efficient heterogeneous catalytic system for Pd-catalyzed allene hydrosilylation towards a wide range of allenes to produce branched allylsilanes with high regioselectivity. The ligand units of the polymer, along with the confinement effect of the porous structure, jointly regulated the regioselectivity. The parts-per-million (ppm) levels of Pd, coordinated with the recyclable heterogeneous ligand, show promise for industrial applications. This work opens a new front of using CMP as an intriguing platform for developing highly efficient catalysts to control the regioselectivities in allene hydrosilylation. The results came from multiple reactions, including the reaction of 2,6-Dibromopyridine(cas: 626-05-1Electric Literature of C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Electric Literature of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem