Month: November 2022

The author of 《Selective C-C bond formation from rhodium-catalyzed C-H activation reaction of 2-arylpyridines with 3-aryl-2H-azirines》 were Baek, Yonghyeon; Kim, Jinwoo; Hyunseok Kim; Jung, Seung Jin; Ryu, Ho; Kim, Suyeon; Son, Jeong-Yu; Um, Kyusik; Han, Sang Hoon; Seo, Hyung Jin; Heo, Juyoung; Lee, Kooyeon; Baik, Mu-Hyun; Lee, Phil Ho. And the article was published in Chemical Science in 2019. Formula: C6H6BrN The author mentioned the following in the article:

A novel method for the synthesis of acylmethyl-substituted 2-arylpyridine derivatives I [R1 = Ph, 4-MeC6H4, 2-ClC6H4, etc.; R2 = 4-Me, 5-C(O)Me, 5-CF3, etc.; R3 = H, Me, F, C(O)Me, CO2Et] was synthesized via rhodium-catalyzed C-H activation reaction of 3-aryl-2H-azirines with 2-arylpyridines and explored a prototype reaction using DFT-calculations Computational studies quickly revealed and prototype exptl. work confirmed that neither the formation of the expected metal nitrene complexes nor the C-N coupling were viable. Instead, azirine ring-opening followed by C-C coupling was found to be much more favorable to give imines that readily underwent hydrolysis in aqueous conditions to form compounds I. This new method was highly versatile and selective toward a wide range of substrates with high functional group tolerance. The results came from multiple reactions, including the reaction of 2-Bromo-5-methylpyridine(cas: 3510-66-5Formula: C6H6BrN)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. Formula: C6H6BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Tuned Al3+ selectivity and π-extended properties of di-2-picolylamine-substituted quinoline-based tolan》 was published in Tetrahedron Letters in 2020. These research results belong to Ko, Min-Sung; Kurapati, Sathish; Jo, Yunhee; Cho, Beomhee; Cho, Dong-Gyu. Name: Bis(pyridin-2-ylmethyl)amine The article mentions the following:

Di-2-picolylamine (DPA)-substituted quinoline-type tolan was synthesized herein. The electron withdrawing CN substituted tolan (1)(I) exhibited clear Al3+ selectivity, unlike simple DPA-substituted quinoline (2). Addnl., owing to the π-extension to quinoline (2), a red shifted fluorescence band and the shoulder of tolan (1) were observed at 491 and 537 nm, resp., whereas the quinoline (2) fluorescence band was observed at approx. 450 nm. Consequently, Al3+ bound tolan was more red shifted in comparison with other metal ions bound by 2. Fluorescence titration of Al3+ to 1 (20μM) in HEPES buffer (10 mM, pH = 7.4) containing 50% MeOH exhibited a limit of detection of 36 nM. The results came from multiple reactions, including the reaction of Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Name: Bis(pyridin-2-ylmethyl)amine)

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. As a tridentate ligand this compound provides three nitrogen donors that affords good selectivity for Zn2+ over biologically relevant metals such as Na+, K+, Mg2+ and Ca2+, and leaves coordination sites free for anion binding. Name: Bis(pyridin-2-ylmethyl)amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Chromium picolinate attenuates cognitive deficit in ICV-STZ rat paradigm of sporadic Alzheimer’s-like dementia via targeting neuroinflammatory and IRS-1/PI3K/AKT/GSK-3β pathway》 was published in Inflammopharmacology in 2020. These research results belong to Akhtar, Ansab; Dhaliwal, Jatinder; Saroj, Priyanka; Uniyal, Ankit; Bishnoi, Mahendra; Sah, Sangeeta Pilkhwal. COA of Formula: C6H5NO2 The article mentions the following:

Alzheimer’s disease (AD) is prevalent in old age people and is one of the most common brain diseases. Brain insulin resistance, neuroinflammation, oxidative stress, and mitochondrial and cholinergic dysfunction are key features of the disease. In our study, streptozotocin (STZ) in a dose of 3 mg/kg was injected in male Wistar rats bilaterally through the intracerebroventricular (ICV) route on stereotaxic apparatus Chromium picolinate (CrPic) was tested at doses of 1 mg/kg, 2 mg/kg, and 4 mg/kg, while rivastigmine (2 mg/kg) was used as reference standard drug. Cognitive dysfunction induced by STZ was assessed by behavioral tests like Morris water maze and novel object recognition test. Treatment with CrPic revealed attenuation of cognitive deficit. STZ-induced neuroinflammation evident by increased TNF-α, IL-6, and CRP levels was also significantly decreased by CrPic. Dysfunctional insulin signaling after ICV-STZ was demonstrated by reduced IRS-1, PI3K, AKT, BDNF gene expression, and increased GSK-3β, NF-κB gene expression with the help of qRT-PCR. CrPic treatment produced an improvement in insulin signaling revealed by increased gene expression of IRS-1, PI3-K, AKT, BDNF, and decreased gene expression of GSK-3β and NF-κB. It was concluded that CrPic reversed AD pathol. revealed by improved memory, reduced oxidative stress, neuroinflammation, mitochondrial dysfunction, and upregulated insulin signaling. The experimental process involved the reaction of Picolinic acid(cas: 98-98-6COA of Formula: C6H5NO2)

Picolinic acid(cas: 98-98-6) is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.COA of Formula: C6H5NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Enantiopure substituted pyridines as promising antimalarial drug candidates》 was published in Tetrahedron in 2020. These research results belong to Bentzinger, Guillaume; Pair, Etienne; Guillon, Jean; Marchivie, Mathieu; Mullie, Catherine; Agnamey, Patrice; Dassonville-Klimpt, Alexandra; Sonnet, Pascal. Formula: C5H3Br2N The article mentions the following:

The enantioselective synthesis and biol. evaluation of 4-(2-amino-1-hydroxyethyl)pyridines I [R1 = n-Bu, n-pentyl, n-hexyl, n-heptyl] as new antimalarial drug candidates was described. In particular, two routes to obtain the key-intermediate 4-vinyl-pyridine were studied. These routes were based on a Krohnke-type cyclization or on metal-catalyzed reactions. The Krohnke-type cyclization route was faster but only efficient at low scale since this pathway involved a Wittig reaction that requires severe temperature-control. Consequently, we designed a second route based on metal-catalyzed reactions. This way was longer but the 4-vinyl-pyridine could be obtained on a 5 g scale at least. Finally, a regioselective SN2 ring-opening of enantiopure epoxides by alkyl primary amines allowed the synthesis of eight I with global yields up to 41%. These compounds showed strong in vitro antimalarial activity against P. falciparum strains and were more active that chloroquine and mefloquine. These results demonstrated that I were promising antimalarial drug candidates. In the experimental materials used by the author, we found 2,6-Dibromopyridine(cas: 626-05-1Formula: C5H3Br2N)

2,6-Dibromopyridine(cas: 626-05-1) 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.Formula: C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《ESI-MS Study of the Interaction of Potential Oxidovanadium(IV) Drugs and Amavadin with Model Proteins》 was published in Inorganic Chemistry in 2020. These research results belong to Ugone, Valeria; Sanna, Daniele; Sciortino, Giuseppe; Crans, Debbie C.; Garribba, Eugenio. Synthetic Route of C6H5NO2 The article mentions the following:

In this study, the binding to lysozyme (Lyz) of four important VIV compounds with antidiabetic and/or anticancer activity, [VIVO(pic)2(H2O)], [VIVO(ma)2], [VIVO(dhp)2], and [VIVO(acac)2], where pic-, ma-, dhp-, and acac- are picolinate, maltolate, 1,2-dimethyl-3-hydroxy-4(1H)-pyridinonate, and acetylacetonate anions, and of the vanadium-containing natural product amavadin ([VIV(hidpa)2]2-, with hidpa3-N-hydroxyimino-2,2′-diisopropionate) was investigated by ElectroSpray Ionization-Mass Spectrometry (ESI-MS). Moreover, the interaction of [VIVO(pic)2(H2O)], chosen as a representative VIVO2+ complex, was examined with two addnl. proteins, myoglobin (Mb) and ubiquitin (Ub), to compare the data. The examined vanadium concentration was in the range 15-150 μM, i.e., very close to that found under physiol. conditions. With pic-, dhp-, and hidpa3-, the formation of adducts n[VIVOL2]-Lyz or n[VIVL2]-Lyz is favored, while with ma- and acac- the species n[VIVOL]-Lyz are detected, with n dependent on the exptl. VIV/protein ratio. The behavior of the systems with [VIVO(pic)2(H2O)] and Mb or Ub is very similar to that of Lyz. The results suggested that under physiol. conditions, the moiety cis-VIVOL2 (L = pic-, dhp-) is bound by only one accessible side-chain protein residue that can be Asp, Glu, or His, while VIVOL+ (L = ma-, acac-) can interact with the two equatorial and axial sites. If the VIV complex is thermodynamically stable and does not have available coordination positions, such as amavadin, the protein cannot interact with it through the formation of coordination bonds and, in such cases, noncovalent interactions are predicted. The formation of the adducts is dependent on the thermodn. stability and geometry in aqueous solution of the VIVO2+ complex and affects the transport, uptake, and mechanism of action of potential V drugs. The potentiality of ElectroSpray Ionization-Mass Spectrometry (ESI-MS) to determine the number and composition of adducts formed by labile V complexes with potential pharmacol. application and the natural product amavadin with some proteins was examined ESI-MS allows the study of vanadium concentrations close to those found under physiol. conditions. The nature of the adducts-which could be related to the transport, uptake, and mechanism of action of potential V drugs-depends on the structure and thermodn. stability at concentrations around micromolar. In the experiment, the researchers used Picolinic acid(cas: 98-98-6Synthetic Route of C6H5NO2)

Picolinic acid(cas: 98-98-6) is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.Synthetic Route of C6H5NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Bis(zinc(II)-dipicolylamine)-functionalized sub-2 μm core-shell microspheres for the analysis of N-phosphoproteome》 was published in Nature Communications in 2020. These research results belong to Hu, Yechen; Jiang, Bo; Weng, Yejing; Sui, Zhigang; Zhao, Baofeng; Chen, Yuanbo; Liu, Lukuan; Wu, Qiong; Liang, Zhen; Zhang, Lihua; Zhang, Yukui. Product Details of 1539-42-0 The article mentions the following:

Protein N-phosphorylation plays a critical role in central metabolism and two/multicomponent signaling of prokaryotes. However, the current enrichment methods for O-phosphopeptides are not preferred for N-phosphopeptides due to the intrinsic lability of P-N bond under acidic conditions. Therefore, the effective N-phosphoproteome anal. remains challenging. Herein, bis(zinc(II)-dipicolylamine)-functionalized sub-2 μm core-shell silica microspheres (SiO2@DpaZn) are tailored for rapid and effective N-phosphopeptides enrichment. Due to the coordination of phosphate groups to Zn(II), N-phosphopeptides can be effectively captured under neutral conditions. Moreover, the method is successfully applied to an E.coli and HeLa N-phosphoproteome study. These results further broaden the range of methods for the discovery of N-phosphoproteins with significant biol. functions. In the experiment, the researchers used many compounds, for example, Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Product Details of 1539-42-0)

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. As a tridentate ligand this compound provides three nitrogen donors that affords good selectivity for Zn2+ over biologically relevant metals such as Na+, K+, Mg2+ and Ca2+, and leaves coordination sites free for anion binding. Product Details of 1539-42-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Redox cycling of copper by coumarin-di(2-picolyl)amine hybrid molecule leads to ROS-mediated modulation of redox scavengers, DNA damage and cell death in diethylnitrosamine induced hepatocellular carcinoma》 was published in Bioorganic Chemistry in 2020. These research results belong to Khan, Saman; Zafar, Atif; Naseem, Imrana. Product Details of 1539-42-0 The article mentions the following:

Targeted therapy is a new strategy for cancer treatment that targets chem. entities specific to cancer cells than normal ones. One of the features associated with malignancy is the elevated copper which plays an integral role in angiogenesis. Work is in progress in our lab to identify new copper chelators to target elevated copper under targeted therapy for the killing of cancer cells. Recently, a coumarin-based copper chelator, di(2-picolyl)amine-3(bromoacetyl)coumarin hybrid mol. (ligand-L) has been synthesized by us, and also studied its copper-dependent macromol. damage response in copper overloaded lymphocytes. The present study investigates the anticancer activity of ligand-L and its mode of action in rat model of diethylnitrosamine (DEN) induced hepatocellular carcinoma. It has been found that liver tissue has a marked increase in copper levels in DEN induced hepatocellular carcinoma. Ex vivo results showed that ligand-L inhibited cell viability, induced reactive oxygen species (ROS) generation, DNA damage, loss of mitochondrial membrane potential and caspase-3 activation in isolated hepatocellular carcinoma cells (HCC). All these effects induced by ligand-L were abrogated by neocuproine and N-acetylcysteine (ROS scavenger). Further, ligand-L treatment of animals bearing hepatocellular carcinoma results in an increment in the cellular redox scavengers, lipid peroxidation and DNA breakage in malignant hepatocytes. In vivo studies using ligand-L also showed that ligand-L possesses anticancer properties as evidenced by improvement in liver marker enzymes and liver surface morphol., and reduced alpha-fetoprotein in the treated group compared to untreated cancer-induced group. Overall, this study suggests that copper-ligand-L interaction leads to ROS generation which caused DNA damage and apoptosis in malignant cells. This study provides enough support to establish ligand-L as a clin. relevant lead mol. for the treatment of different malignancies. In the experiment, the researchers used many compounds, for example, Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Product Details of 1539-42-0)

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. As a tridentate ligand this compound provides three nitrogen donors that affords good selectivity for Zn2+ over biologically relevant metals such as Na+, K+, Mg2+ and Ca2+, and leaves coordination sites free for anion binding. Product Details of 1539-42-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Enantioselective Synthesis of 4-Cyanotetrahydroquinolines via Ni-Catalyzed Hydrocyanation of 1,2-Dihydroquinolines》 was published in Organic Letters in 2020. These research results belong to Jiao, Mingdong; Gao, Jihui; Fang, Xianjie. HPLC of Formula: 197958-29-5 The article mentions the following:

A Ni-catalyzed asym. hydrocyanation that enables the formation of 4-cyanotetrahydroquinolines in good yields with excellent enantioselectivities is presented herein. A variety of functional groups are well-tolerated, and a gram-scale reaction supports the synthetic potential of the transformation. Addnl., several crucial intermediates for pharmaceutically active agents, including a PGD2 receptor antagonist, are now accessible through asym. synthesis using this new protocol. In the part of experimental materials, we found many familiar compounds, such as 2-Pyridinylboronic acid(cas: 197958-29-5HPLC of Formula: 197958-29-5)

2-Pyridinylboronic acid(cas: 197958-29-5) 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. HPLC of Formula: 197958-29-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Aza-Henry Reaction: Synthesis of Nitronaphthylamines from 2-(Alkynyl)benzonitriles》 was written by Verma, Shalini; Kumar, Manoj; Verma, Akhilesh K.. Reference of 2-Bromonicotinaldehyde And the article was included in Organic Letters in 2020. The article conveys some information:

A transition-metal-free approach for construction of nitronaphthylamines has been developed for the first time through aza-henry, chemoselective, and regioselective annulation of 2-alkynylbenzonitriles with nitromethane. In addition, the strategy provides an elegant, operationally simple and atom-economical route for the synthesis of nitroamino substituted heterocyclic scaffolds, featuring a range of sensitive functional groups. The reaction could also devise acetonitrile and acetophenone as nucleophile. The protocol has been successfully implemented for late-stage modification of bioactive mols.2-Bromonicotinaldehyde(cas: 128071-75-0Reference of 2-Bromonicotinaldehyde) was used in this study.

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. When pyridine is adsorbed on oxide surfaces or in porous materials, the following species are commonly observed: (i) pyridine coordinated to Lewis acid sites, (ii) pyridine H-bonded to weakly acidic hydroxyls, and (iii) protonated pyridine. At high coverage, physisorbed pyridine and protonated dimers can also be observed.Reference of 2-Bromonicotinaldehyde

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ponpao, Nipaphorn; Senapak, Warapong; Saeeng, Rungnapha; Jaratjaroonphong, Jaray; Sirion, Uthaiwan published their research in RSC Advances in 2021. The article was titled 《Metal- and solvent-free synthesis of aniline- and phenol-based triarylmethanes via Bronsted acidic ionic liquid catalyzed Friedel-Crafts reaction》.Synthetic Route of C6H4BrNO The article contains the following contents:

A beneficial, scalable and efficient methodol. for the synthesis of aniline-based triarylmethanes was established through the double Friedel-Crafts reaction of com. aldehydes and primary, secondary or tertiary anilines using Bronsted acidic ionic liquid as a powerful catalyst, namely [bsmim][NTf2] (4-sulfono-1-butylmethylimidazolium trifluoromethanesulfonimide). This protocol was successfully performed under metal- and solvent-free conditions with a broad range of substrates, giving the corresponding aniline-based triarylmethane products in good to excellent yields (up to 99%). In addition, alternative aromatic nucleophiles such as phenols and electron-rich arenes were also studied using this useful approach to achieve a diversity of triarylmethane derivatives in high to excellent yields. The results came from multiple reactions, including the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0Synthetic Route of C6H4BrNO)

2-Bromonicotinaldehyde(cas: 128071-75-0) 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.Synthetic Route of C6H4BrNO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem