Zhou, Min’s team published research in Angewandte Chemie, International Edition in 2020 | CAS: 3510-66-5

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Product Details of 3510-66-5

Product Details of 3510-66-5In 2020 ,《Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings》 was published in Angewandte Chemie, International Edition. The article was written by Zhou, Min; Tsien, Jet; Qin, Tian. The article contains the following contents:

Despite the tremendous utilities of metal-mediated cross-couplings in modern organic chem., coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking – coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, the authors report a sulfur (IV) mediated cross-coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily-accessible alkyl sulfinyl (IV) chloride gave a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion. The experimental process involved the reaction of 2-Bromo-5-methylpyridine(cas: 3510-66-5Product Details of 3510-66-5)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Product Details of 3510-66-5

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ma, Yueyue’s team published research in Angewandte Chemie, International Edition in 2019 | CAS: 100-48-1

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Quality Control of 4-Cyanopyridine

Quality Control of 4-CyanopyridineIn 2019 ,《Direct Arylation of α-Amino C(sp3)-H Bonds by Convergent Paired Electrolysis》 was published in Angewandte Chemie, International Edition. The article was written by Ma, Yueyue; Yao, Xiantong; Zhang, Lei; Ni, Pufan; Cheng, Ruihua; Ye, Jinxing. The article contains the following contents:

A metal-free convergent paired electrolysis strategy to synthesize benzylic amines through direct arylation of tertiary amines and benzonitrile derivatives at room temperature was developed. This TEMPO-mediated electrocatalytic reaction made full use of both anodic oxidation and cathodic reduction without metals or stoichiometric oxidants, thus showing great potential and advantages for practical synthesis. This convergent paired electrolysis method provided a straightforward and powerful means to activate C-H bonds and realize cross-coupling with cathodically generated species. The experimental process involved the reaction of 4-Cyanopyridine(cas: 100-48-1Quality Control of 4-Cyanopyridine)

4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Quality Control of 4-Cyanopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Liu, Jianming’s team published research in Asian Journal of Organic Chemistry in 2020 | CAS: 128071-75-0

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Application In Synthesis of 2-Bromonicotinaldehyde

Application In Synthesis of 2-BromonicotinaldehydeIn 2020 ,《Elemental Sulfur-Promoted [2+3+1] Annulation for Synthesis of Functionalized Thiochromeno[2,3-b]indoles from Indole Derivatives》 was published in Asian Journal of Organic Chemistry. The article was written by Liu, Jianming; Wang, Zhixian; Wang, Ke; Liu, Dong; Yang, Yan; Fan, Junjun; Zhuo, Kelei; Yue, Yuanyuan. The article contains the following contents:

An intermol. [2+3+1] annulation between indoles I (R1 = H, Me, OMe, Cl, Br; R2 = H, Me, F, OMe, Cl, Br; R3 = H, Me, Cl, F; R4 = H, OMe, Br, Cl) and aromatic aldehyde derivatives 2-Br-3-R5-4-R6-5-R7C6HCHO (R5 = H; R6 = H, Me; R7 = H, F, CF3; R5R6 = -CH=CH-CH=CH-) and 2-bromonicotinaldehyde was successfully achieved by utilizing elemental sulfur as the promoter and coupling partner. This direct and operationally simple procedure provided a rapid and reliable approach to synthesize functionalized thiochromeno[2,3-b]indoles II and pyrido[3′, 2′:5,6]thiopyrano[2, 3-b]indoles III. Preliminary mechanistic studies indicated that elemental sulfur enhanced the nucleophilicity of the 3-position of indole to attack an aldehyde group, and C-H cleavage of indole was not involved in the rate-determining step. The results came from multiple reactions, including the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0Application In Synthesis of 2-Bromonicotinaldehyde)

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Application In Synthesis of 2-Bromonicotinaldehyde

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Nakamura, Shuichi’s team published research in Chemistry – A European Journal in 2010 | CAS: 410092-98-7

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. COA of Formula: C35H27N3O2The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

《Copper-Catalyzed Enantioselective Three-Component Synthesis of Optically Active Propargylamines from Aldehydes, Amines, and Aliphatic Alkynes》 was published in Chemistry – A European Journal in 2010. These research results belong to Nakamura, Shuichi; Ohara, Mutsuyo; Nakamura, Yuko; Shibata, Norio; Toru, Takeshi. COA of Formula: C35H27N3O2 The article mentions the following:

An enantioselective three-component reaction of aldehydes, amines, and aliphatic alkynes catalyzed by C2-sym. pybim Cu1 catalysts to give propargylamines, e.g., I in good yields and with high enantioselectivity has been developed. This process has many advantages, such as simplified operation and mild reaction conditions. These results open a novel way to synthesize optically active propargylamines. In the experiment, the researchers used many compounds, for example, 2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7COA of Formula: C35H27N3O2)

2,6-Bis((4S,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine(cas: 410092-98-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. COA of Formula: C35H27N3O2The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Habermeyer, Benoit’s team published research in Chemistry – A European Journal in 2011 | CAS: 29682-15-3

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Electric Literature of C7H6BrNO2

《Dynamics of Closure of a Zinc Bis-Porphyrin Molecular Tweezers with Copper(II) Ions and Electron Transfer》 was written by Habermeyer, Benoit; Takai, Atsuro; Gros, Claude P.; El Ojaimi, Maya; Barbe, Jean-Michel; Fukuzumi, Shun-Ichi. Electric Literature of C7H6BrNO2This research focused onzinc bisporphyrin mol tweezer copper amine imine spacer preparation; mol tweezer zinc bisporphyrin copper complexation electron transfer; redox potential zinc bisporphyrin mol tweezer copper coordination closure; electrochem redox zinc bisporphyrin mol tweezer copper coordination. The article conveys some information:

Zinc bis-porphyrin mol. tweezers composed of a N4 spacer bound through pyridyl units to the meso position of porphyrins were synthesized, and the tweezers are closed by the coordination of a Cu(II) ion inside the spacer ligand. The effect of the π-π interaction between the porphyrin rings in the closed conformation on the absorption spectra of multi-electron oxidized species and the reduction potentials were clarified by chem. and electrochem. oxidation of the closed form of the zinc bis-porphyrin mol. tweezers in comparison with the open form without Cu(II) ion and the corresponding porphyrin monomer. The shifts in redox potentials and absorption spectrum of the porphyrin dication indicate a strong electronic interaction between the two oxidized porphyrins in the closed form, whereas there is little interaction between them in the neutral form. The dynamics of Cu(II) ion coordination and subsequent electron transfer was examined by using a stopped-flow UV/visible spectroscopic technique. Coordination of Cu(II) occurs prior to electron-transfer oxidation of the closed form of the zinc bis-porphyrin mol. tweezers. In the experimental materials used by the author, we found Methyl 5-bromopicolinate(cas: 29682-15-3Electric Literature of C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Electric Literature of C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Li, Qiang’s team published research in Advanced Therapeutics (Weinheim, Germany) in 2018 | CAS: 103-74-2

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.HPLC of Formula: 103-74-2

《Near-Infrared Fluorescent Theranostic Cisplatin Prodrug with Transcatheter Intra-Arterial Therapy: Application to Rabbit Hepatocellular Carcinoma》 was written by Li, Qiang; Wang, Qi; Wang, Saibo; Zhu, Shiqin; Yuan, Tianwen; Guo, Zhiqian; Cao, Jun; Tian, He; Zhu, Wei-Hong. HPLC of Formula: 103-74-2This research focused ontranscatheter intra arterial therapy cisplatin prodrug hepatocellular carcinoma. The article conveys some information:

Transcatheter intra-arterial therapy (TIT) has become valuable in the battle against primary and secondary hepatic malignancies. However, the lack of a mechanism to visualize real-time drug release and avoid fast metabolic clearance of chemotherapeutic agents is the primary barrier to TIT for hepatocellular carcinoma. Here, a specific near-IR (NIR) fluorescent prodrug platform, i.e., DSPE-mPEG/DCM-S-Pt micelles (DCM-S-Pt@PEG), to assist TIT in direct administration to large mammals like rabbits, is presented. DCM-S-Pt@PEG consists of a NIR fluorophore for tracing drug release, a nonspecific antitumor drug cisplatin for hepatocellular carcinoma treatment, a glutathione-activatable disulfide linker, and a DSPE-mPEG nano-micelle carrier for controllable drug release. DCM-S-Pt@PEGcan make the drug accumulation in tumor tissues enhance the therapeutic effect by: (i) specific delivery of prodrug to hepatic tumor tissues through the femoral artery by TIT, (ii) sustained drug-release from the biodegradable lipid DSPE-mPEG micelle to minimize metabolic clearance, and (iii) cancer biomarker-activated drug release. It provides a promising strategy to assist TIT in treating unresectable devastating hepatocellular carcinoma administration in the rabbit model, rather than common mouse model. In the experiment, the researchers used 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2HPLC of Formula: 103-74-2)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.HPLC of Formula: 103-74-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ward, Richard A.’s team published research in Journal of Medicinal Chemistry in 2017 | CAS: 1365836-53-8

(6-Methylpyridin-2-yl)methanamine hydrochloride(cas: 1365836-53-8) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Related Products of 1365836-53-8

《Structure-Guided Discovery of Potent and Selective Inhibitors of ERK1/2 from a Modestly Active and Promiscuous Chemical Start Point》 was written by Ward, Richard A.; Bethel, Paul; Cook, Calum; Davies, Emma; Debreczeni, Judit E.; Fairley, Gary; Feron, Lyman; Flemington, Vikki; Graham, Mark A.; Greenwood, Ryan; Griffin, Nicola; Hanson, Lyndsey; Hopcroft, Philip; Howard, Tina D.; Hudson, Julian; James, Michael; Jones, Clifford D.; Jones, Christopher R.; Lamont, Scott; Lewis, Richard; Lindsay, Nicola; Roberts, Karen; Simpson, Iain; St-Gallay, Steve; Swallow, Steve; Tang, Jia; Tonge, Michael; Wang, Zhenhua; Zhai, Baochang. Related Products of 1365836-53-8 And the article was included in Journal of Medicinal Chemistry on April 27 ,2017. The article conveys some information:

There are a number of small-mol. inhibitors targeting the RAS/RAF/MEK/ERK signaling pathway that have either been approved or are in clin. development for oncol. across a range of disease indications. The inhibition of ERK1/2 is of significant current interest, as cell lines with acquired resistance to BRAF and MEK inhibitors have been shown to maintain sensitivity to ERK1/2 inhibition in preclin. models. This article reports on authors’ recent work to identify novel, potent, and selective reversible ERK1/2 inhibitors from a low-mol.-weight, modestly active, and highly promiscuous chem. start point, compound I. To guide and inform the evolution of this series, inhibitor binding mode information from X-ray crystal structures was critical in the rapid exploration of this template to compound II, which was active when tested in in vivo antitumor efficacy experiments After reading the article, we found that the author used (6-Methylpyridin-2-yl)methanamine hydrochloride(cas: 1365836-53-8Related Products of 1365836-53-8)

(6-Methylpyridin-2-yl)methanamine hydrochloride(cas: 1365836-53-8) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Related Products of 1365836-53-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Morisawa, Yasuhiro’s team published research in Journal of Medicinal Chemistry in 1977 | CAS: 59290-82-3

3-Nitroisonicotinic acid(cas: 59290-82-3) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Electric Literature of C6H4N2O4

《Studies on anticoccidial agents. 11. Synthesis and anticoccidial activity of nitropyridinecarboxamides and derivatives》 was published in Journal of Medicinal Chemistry in 1977. These research results belong to Morisawa, Yasuhiro; Kataoka, Mitsuru; Kitano, Noritoshi. Electric Literature of C6H4N2O4 The article mentions the following:

Of 56 title compounds prepared, optimal in vivo activity against Eimeria tenella was shown by 2-nitroisonicotinamide (I, R1 = R2 = H) [60780-17-8] and 11 derivatives (I: R1 = H, Me; R2 = Me, CH2OH, alkanoyl, aryl acyl, heterocyclic acyl). Activity was shown by 2-, 3-, 5-, and 6-nitro-, but not by 4-nitropyridinecarboxamides. Substitution on the amide N of the various positional isomers affected their activity differently. In the part of experimental materials, we found many familiar compounds, such as 3-Nitroisonicotinic acid(cas: 59290-82-3Electric Literature of C6H4N2O4)

3-Nitroisonicotinic acid(cas: 59290-82-3) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Electric Literature of C6H4N2O4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Ibrahim, Inam Hassim’s team published research in Systematic Reviews in Pharmacy in 2021 | CAS: 141-86-6

2,6-Diaminopyridine(cas: 141-86-6) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Formula: C5H7N3

《Synthesis and characterization of fluorescent Schiff bases and their metal complexes from 9-anthracenecarboxaldehy》 was written by Ibrahim, Inam Hassim; Hasan, Hasan A.. Formula: C5H7N3This research focused ontransition metal complex fluorescent Schiff base analysis. The article conveys some information:

Synthesis and characterization two Schiff bases[L1] (N2Z,N6Z)-N2,N6-bis(4-((E)-anthracen-9-ylmethyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-ylidene)pyridine-2,6-diamine Synthesis via reaction of 2,6-diaminopyridine, 4-aminoantipyrine and 9-anthracenecarboxaldehyde with mole ratio (1:2:2) resp. two steps. And [L2] (N1Z,N2Z)-N1,N2-bis(4-((E)-anthracen-9-ylmethyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-ylidene)-4-methylbenzene-1,2-diamine Synthesis from reaction of o-phenylendiamine, 4-aminoantipyrine and 9-anthracenecarboxaldehyde with mole ratio (1:2:2) resp. two steps. A new series of transition metal complexes of Mn(II), Co(II), Ca(II), Cd(II), Zn(II) and pd(II) were synthesized. The structural features were derived from their elemental analyses, IR, UV-visible spectroscopy, 1HNMR, 13CNMR spectroscopy, thermal gravimetric analyses spectral, magnetic susceptibility measurement, chloride content and conductivity measurements. The electronic spectral data and magnetic measurements indicate that the complexes exhibit octahedral geometry around Ca(II), Mn(II), Cd(II), Co(II), Zn(II) while Square planer geometry around Pd(II). In addition to this study using 2,6-Diaminopyridine, there are many other studies that have used 2,6-Diaminopyridine(cas: 141-86-6Formula: C5H7N3) was used in this study.

2,6-Diaminopyridine(cas: 141-86-6) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Formula: C5H7N3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Pengtao’s team published research in Bioorganic & Medicinal Chemistry in 2013 | CAS: 1179360-43-0

3-Chloropicolinimidamide hydrochloride(cas: 1179360-43-0) 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.Related Products of 1179360-43-0

Related Products of 1179360-43-0On May 1, 2013 ,《Pyridinylpyrimidines selectively inhibit human methionine aminopeptidase-1》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Zhang, Pengtao; Yang, Xinye; Zhang, Feiran; Gabelli, Sandra B.; Wang, Renxiao; Zhang, Yihua; Bhat, Shridhar; Chen, Xiaochun; Furlani, Manuel; Amzel, L. Mario; Liu, Jun O.; Ma, Dawei. The article conveys some information:

Cellular protein synthesis is initiated with methionine in eukaryotes with few exceptions. Methionine aminopeptidases (MetAPs) which catalyze the process of N-terminal methionine excision are essential for all organisms. In mammals, type 2 MetAP (MetAP2) is known to be important for angiogenesis, while type 1 MetAP (MetAP1) has been shown to play a pivotal role in cell proliferation. Authors’ previous high-throughput screening of a com. compound library uncovered a novel class of inhibitors for both human MetAP1 (HsMetAP1) and human MetAP2 (HsMetAP2). This class of inhibitors contains a pyridinylpyrimidine core. To understand the structure-activity relationship (SAR) and to search for analogs of 2 with greater potency and higher HsMetAP1-selectivity, a total of 58 analogs were acquired through either com. source or by inhouse synthesis and their inhibitory activities against HsMetAP1 and HsMetAP2 were determined Through this systematic medicinal chem. anal., the authors have identified: (1) 5-chloro-6-methyl-2-pyridin-2-ylpyrimidine as the min. element for the inhibition of HsMetAP1; (2) 5′-chloro as the favored substituent on the pyridine ring for the enhanced potency against HsMetAP1; and (3) long C4 side chains as the essentials for higher HsMetAP1-selectivity. As a result of the SAR campaign, six compounds were found to be among the most selective and potent inhibitors of purified HsMetAP1 reported to date. In addition, crystallog. anal. of one representative inhibitor (I) in complex with N-terminally truncated HsMetAP1 was also performed. Map gene.3-Chloropicolinimidamide hydrochloride(cas: 1179360-43-0Related Products of 1179360-43-0) was used in this study.

3-Chloropicolinimidamide hydrochloride(cas: 1179360-43-0) 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.Related Products of 1179360-43-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem