Month: October 2022

Zheng, Shuyuan; Han, Jianlei; Jin, Xue; Ye, Qiang; Zhou, Jin; Duan, Pengfei; Liu, Minghua published an article in 2021. The article was titled 《Halogen Bonded Chiral Emitters: Generation of Chiral Fractal Architecture with Amplified Circularly Polarized Luminescence》, and you may find the article in Angewandte Chemie, International Edition.Synthetic Route of C7H5N The information in the text is summarized as follows:

Self-assembled chiroptical materials have attracted considerable attention due to their great applications in wide fields. During the chiral self-assembly, it remains unknown how achiral mols. can affect the assembly process and their final chiroptical performance. Herein, the authors report an achiral mol. directed chiral self-assembly via halogen bonds, exhibiting not only an unprecedented chiral fractal architecture but also significantly amplified circularly polarized luminescence (CPL). Two axially chiral emitters with halogen bond sites co-assemble with an achiral 1,4-diiodotetrafluorobenzene (F4DIB) and well-ordered chiral fractal structures with asymmetry amplification are obtained. The enhancement of the dissymmetry factors of the assemblies was ≤0.051 and ≤0.011, which was ∼100 folds than those of the corresponding mols. Both the design of the chiral emitter and the highly directional halogen bond played an important role in hierarchically chirality transfer from chiral emitters to the micrometer scale chiral fractal morphol. and amplified dissymmetry factors. The authors hope that this strategy can give a further insight into the fabrication of structurally unique featured highly efficient chiroptical materials. The experimental part of the paper was very detailed, including the reaction process of 4-Ethynylpyridine(cas: 2510-22-7Synthetic Route of C7H5N)

4-Ethynylpyridine(cas: 2510-22-7) 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. Synthetic Route of C7H5N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lai, Miao; Su, Fangyao; Hu, Jingyi; Wang, Mengzhuo; Zhao, Mingqin; Zhang, Ganlin published an article in 2021. The article was titled 《Synthesis of N-heteroarenemethyl esters via C-C bond cleavage of acyl cyanides under transition metal-free conditions》, and you may find the article in Frontiers in Chemistry (Lausanne, Switzerland).Quality Control of 2-(2-Hydroxyethyl)pyridine The information in the text is summarized as follows:

A practical method to synthesize N-heteroaryl esters from N-heteroaryl methanols with acyl cyanides via C-C bond cleavage without using any transition metal is demonstrated here. The use of Na2CO3/15-crown-5 couple enables access to a series of N-heteroaryl esters in high efficiency. This protocol is operationally simple and highly environmentally benign producing only cyanides as byproducts. The results came from multiple reactions, including the reaction of 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Quality Control of 2-(2-Hydroxyethyl)pyridine)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) 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. Quality Control of 2-(2-Hydroxyethyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Duan, Ying-Chao; Jin, Lin-Feng; Ren, Hong-Mei; Zhang, Shao-Jie; Liu, Yue-Jiao; Xu, Yong-Tao; He, Zi-Hao; Song, Yu; Yuan, Hang; Chen, Shu-Hui; Guan, Yuan-Yuan published an article in 2021. The article was titled 《Design, synthesis, and biological evaluation of novel dual inhibitors targeting lysine specific demethylase 1 (LSD1) and histone deacetylases (HDAC) for treatment of gastric cancer》, and you may find the article in European Journal of Medicinal Chemistry.Safety of Pyridin-3-ylboronic acid The information in the text is summarized as follows:

A series of novel LSD1/HDAC bifunctional inhibitors with a styrylpyridine skeleton I [meta-, para-substituted; X = CH, N; R = H, 3-thienyl, 2-hydroxy-5-fluorophenyl, etc; R1 = H, F], II and III [R2 = H, F; R3 = H, Me, F3C; R4 = H, F, HO, MeO] were designed and synthesized based on our previously reported LSD1 inhibitors. The representative compounds I [para-substituted; X = N; R = 2-hydroxyphenyl, 2-fluoro-4-methylphenyl; R1 = H] showed potent activity against LSD1 and HDAC at both mol. and cellular level and displayed high selectivity against MAO-A/B. Compounds I [para-substituted; X = N; R = 2-hydroxyphenyl, 2-fluoro-4-methylphenyl; R1 = H] demonstrated potent antiproliferative activities against MGC-803 and HCT-116 cancer cell lines. Compound I [para-substituted, X = N, R = 2-fluoro-4-methylphenyl, R1 = H] showed superior in-vitro anticancer potency against a panel of gastric cancer cell lines than ORY-1001 and SP-2509 with IC50 values ranging from 0.23 to 1.56μM. Compounds I [para-substituted; X = N; R = 2-hydroxyphenyl, 2-fluoro-4-methylphenyl; R1 = H] significantly modulated the expression of Bcl-2, Bax, Vimentin, ZO-1 and E-cadherin, induced apoptosis, reduced colony formation and suppressed migration in MGC-803 cancer cells. In addition, preliminary absorption, distribution, metabolism, excretion (ADME) studies revealed that compounds I [para-substituted; X = N; R = 2-hydroxyphenyl, 2-fluoro-4-methylphenyl; R1 = H] showed acceptable metabolic stability in human liver microsomes with minimal inhibition of cytochrome P450s (CYPs). Those results indicated that compound I [para-substituted, X = N, R = 2-fluoro-4-methylphenyl, R1 = H] could be a promising lead compound for further development as a therapeutic agent in gastric cancers via LSD1 and HDAC dual inhibition. In the part of experimental materials, we found many familiar compounds, such as Pyridin-3-ylboronic acid(cas: 1692-25-7Safety of Pyridin-3-ylboronic acid)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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. Safety of Pyridin-3-ylboronic acid

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Khatua, Hillol; Das, Sandip Kumar; Roy, Satyajit; Chattopadhyay, Buddhadeb published an article in 2021. The article was titled 《Dual Reactivity of 1,2,3,4-Tetrazole: Manganese-Catalyzed Click Reaction and Denitrogenative Annulation》, and you may find the article in Angewandte Chemie, International Edition.Formula: C6H6BrN The information in the text is summarized as follows:

A general catalytic method using a Mn-porphyrin-based catalytic system is reported that enables two different reactions (click reaction and denitrogenative annulation) and affords two different classes of nitrogen heterocycles, 1,5-disubstituted 1,2,3-triazoles (with a pyridyl motif) and 1,2,4-triazolo-pyridines. Mechanistic studies suggest that although the click reaction likely proceeds through an ionic mechanism, which is different from the traditional click reaction, the denitrogenative annulation reaction likely proceeds via an electrophilic metallonitrene intermediate rather than a metalloradical intermediate. Collectively, this method is highly efficient and offers several advantages over other methods. For example, this method excludes a multi-step synthesis of the N-heterocyclic mols. described and produces only environmentally benign N2 gas a byproduct. In the experiment, the researchers used many compounds, for example, 2-Bromo-5-methylpyridine(cas: 3510-66-5Formula: C6H6BrN)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Formula: C6H6BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tarzia, Andrew; Lewis, James E. M.; Jelfs, Kim E. published an article in 2021. The article was titled 《High-Throughput Computational Evaluation of Low Symmetry Pd2L4 Cages to Aid in System Design》, and you may find the article in Angewandte Chemie, International Edition.Recommanded Product: 1692-25-7 The information in the text is summarized as follows:

Unsym. ditopic ligands can self-assemble into reduced-symmetry Pd2L4 metallo-cages with anisotropic cavities, with implications for high specificity and affinity guest-binding. Mixtures of cage isomers can form, however, resulting in undesirable system heterogeneity. It is paramount to be able to design components that preferentially form a single isomer. Previous data suggested that computational methods could predict with reasonable accuracy whether unsym. ligands would preferentially self-assemble into single cage isomers under constraints of geometrical mismatch. Authors successfully apply a collaborative computational and exptl. workflow to mitigate costly trial-and-error synthetic approaches. Their rapid computational workflow constructs unsym. ligands and their Pd2L4 cage isomers, ranking the likelihood for exclusively forming cis-Pd2L4 assemblies. From this narrowed search space, we successfully synthesized four new, low-symmetry, cis-Pd2L4 cages. In the experiment, the researchers used many compounds, for example, Pyridin-3-ylboronic acid(cas: 1692-25-7Recommanded Product: 1692-25-7)

Pyridin-3-ylboronic acid(cas: 1692-25-7) 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.Recommanded Product: 1692-25-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wang, Peng-Fei; Yu, Jiao; Guo, Kai-Xin; Jiang, Sheng-Peng; Chen, Ji-Jun; Gu, Qiang-Shuai; Liu, Ji-Ren; Hong, Xin; Li, Zhong-Liang; Liu, Xin-Yuan published an article in 2022. The article was titled 《Design of Hemilabile N,N,N-Ligands in Copper-Catalyzed Enantioconvergent Radical Cross-Coupling of Benzyl/Propargyl Halides with Alkenylboronate Esters》, and you may find the article in Journal of the American Chemical Society.Application of 2510-22-7 The information in the text is summarized as follows:

The enantioconvergent radical C(sp3)-C(sp2) cross-coupling of alkyl halides with alkenylboronate esters is an appealing tool in the assembly of synthetically valuable enantioenriched alkenes owing to the ready availability, low toxicity and air/moisture stability of alkenylboronate esters. A copper/chiral N,N,N-ligand catalytic system for the enantioconvergent cross-coupling of benzyl/propargyl halides with alkenylboronate esters (>80 examples) with good functional group tolerance was reported. The key to the success was the rational design of hemilabile N,N,N-ligands by mounting steric hindrance at the ortho position of one coordinating quinoline ring. Thus, the newly designed ligand not only promote the radical cross-coupling process in the tridentate form but also delivered enantiocontrol over highly reactive alkyl radicals in the bidentate form. Facile follow-up transformations highlight its potential utility in the synthesis of various enantioenriched building blocks as well as in the late-stage functionalization for drug discovery.4-Ethynylpyridine(cas: 2510-22-7Application of 2510-22-7) was used in this study.

4-Ethynylpyridine(cas: 2510-22-7) 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 of 2510-22-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Wang, Ze-Shu; Zhu, Lu-Jing; Li, Cui-Ting; Liu, Bin-Yang; Hong, Xin; Ye, Long-Wu published an article in Angewandte Chemie, International Edition. The title of the article was 《Synthesis of Axially Chiral N-Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Broensted Acids》.Recommanded Product: 128071-75-0 The author mentioned the following in the article:

In recent years, asym. catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble-metal catalysis. Herein, a facile access to axially chiral N-heterocycles enabled by chiral Broensted acid-catalyzed 5-endo-dig cyclization of ynamides is disclosed, which represents the first metal-free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom-economical synthesis of valuable N-arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N-arylindole skeletons are demonstrated to be applicable to asym. catalysis. The results came from multiple reactions, including the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0Recommanded Product: 128071-75-0)

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Recommanded Product: 128071-75-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2022,Gottwald, Dominique; Geidel, Christian; Rueffer, Tobias; Schaarschmidt, Dieter; Lang, Heinrich published an article in Journal of Organometallic Chemistry. The title of the article was 《Heterodi-, -tri- and -tetrametallic Transition-Metal-Complexes》.Safety of 4-Ethynylpyridine The author mentioned the following in the article:

Complexes trans-[Pt(CCMc)2(PBu3)2] (Mc = Fc = Fe(n5-C5H4)(n5-C5H5) (3), [1,2] Mc = Rc = Ru(n5-C5H4)(n5-C5H5) (4)) were synthesized by treatment of cis-[PtCl2(PBu3)2] with McCCH (Mc = Fc (1), Rc (2)). The synthesis of trans-[Pt(PR3)2(CCFc)(CCR’)] (R = Bu: R’ = H (7a), R’ = PPh2 (7b), R’ = Rc (7c); R = Ph: R’ = 4-C5H4N (8a), R’ = C6H4-4-CN (8b), R’ = 2,2′-bipyridin-5-yl (8c), R’ = C6H4-4-CCH (8d)) was realized by the reaction of trans-[PtCl(PR3)2(CCFc)] (R = Bu (5), R = Ph (6)) with alkynes HCCR’. Treatment of 8a with [RuCl2(cymene)]2 (cymene = η6-1-Me-4-iPr-C6H4) or [Rh(η5-C5Me5)Cl2]2 and of 8c with [Mo(CO)4(2,5-norbornadiene)] or [Mn(CO)5Br] led to heterotrimetallic trans-[Pt(PPh3)2(CCFc)(CCR’-{M})] (R’ = 4-C5H4N: {M} = Ru(η6-cymene)Cl2 (10a), = Rh(η5-C5Me5)Cl2 (10b); R’ = 2,2′-bipyridin-5-yl: {M} = Mo(CO)4 (11a), = Mn(CO)3Br (11b)). When 8b,c were reacted with [{[Ti](μ-σ,π-CCSiMe3)2}Cu(MeCN)][PF6] ([Ti] = Ti(η5-C5H4SiMe3)2) then heterotetrametallic trans-[Pt(PPh3)2(CCFc)(CCR’-{M})][PF6] {M} = [Ti](μ-σ,π-CCSiMe3)2Cu: R’ = 2,2′-bipyridin-5-yl (11c), R’ = -C6H4-4-CN (11d) were produced. Compounds 3, 4 and 7c were characterized by single-crystal X-ray diffraction studies establishing the trans arrangement at Pt. The electrochem. behavior of all compounds was investigated by CV showing reversible redox events for Fc in 3, 7a,c, 8a-d, 10a,b, 11b,c in the range of E°1′ = -120 – -85 mV, while M feature irreversible redox processes between 745 and 1230 mV. In addition to this study using 4-Ethynylpyridine, there are many other studies that have used 4-Ethynylpyridine(cas: 2510-22-7Safety of 4-Ethynylpyridine) was used in this study.

4-Ethynylpyridine(cas: 2510-22-7) 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. Safety of 4-Ethynylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

SDS of cas: 29682-15-3In 1982 ,《Reactions of haloquinolizinium bromides with diethylamine》 appeared in Journal of Heterocyclic Chemistry. The author of the article were Sanders, Georgine M.; Van Dijk, M.; Van der Plas, H. C.. The article conveys some information:

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. The results came from multiple reactions, including the reaction of Methyl 5-bromopicolinate(cas: 29682-15-3SDS of cas: 29682-15-3)

Methyl 5-bromopicolinate(cas: 29682-15-3) 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. SDS of cas: 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Computed Properties of C6H7Br2NIn 2017 ,《Discovery of Allosteric Inhibitors Targeting the Spliceosomal RNA Helicase Brr2》 was published in Journal of Medicinal Chemistry. The article was written by Iwatani-Yoshihara, Misa; Ito, Masahiro; Klein, Michael G.; Yamamoto, Takeshi; Yonemori, Kazuko; Tanaka, Toshio; Miwa, Masanori; Morishita, Daisuke; Endo, Satoshi; Tjhen, Richard; Qin, Ling; Nakanishi, Atsushi; Maezaki, Hironobu; Kawamoto, Tomohiro. The article contains the following contents:

Brr2 is an RNA helicase belonging to the Ski2-like subfamily and an essential component of spliceosome. Brr2 catalyzes an ATP-dependent unwinding of the U4/U6 RNA duplex, which is a critical step for spliceosomal activation. An HTS campaign using an RNA-dependent ATPase assay and initial SAR study identified two different Brr2 inhibitors, 3 (I) and 12 (II). Cocrystal structures revealed 3 binds to an unexpected allosteric site between the C-terminal and the N-terminal helicase cassettes, while 12 binds an RNA-binding site inside the N-terminal cassette. Selectivity profiling indicated the allosteric inhibitor 3 is more Brr2-selective than the RNA site binder 12. Chem. optimization of 3 using SBDD culminated in the discovery of the potent and selective Brr2 inhibitor 9 (III) with helicase inhibitory activity. The authors’ findings demonstrate an effective strategy to explore selective inhibitors for helicases, and 9 could be a promising starting point for exploring mol. probes to elucidate biol. functions and the therapeutic relevance of Brr2. In the experiment, the researchers used 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Computed Properties of C6H7Br2N)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. Computed Properties of C6H7Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem