Month: December 2022

Pastor, Stephen D. published the artcileSubstituted 5-(D,L-erythro-1′,2′-dihydroxypropyl)pyrazines. Potential precursors for the synthesis of biopterin derivatives, Application In Synthesis of 5098-14-6, the publication is Journal of Heterocyclic Chemistry (1984), 21(3), 657-60, database is CAplus.

Substituted 5-(D,L–erythro-1′,2′-dihydroxypropyl)pyrazines I (R = cyano, CO₂CH₂Ph) were prepared from crotonic acid. Functionalized 2-oximino-3-oxoesters II (R¹ = Me, CMe₃) showed anomalous behavior during decarboxylation. The structures of prepared compounds were determined by spectroscopic methods.

Journal of Heterocyclic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Application In Synthesis of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Maity, Soham published the artcileStereoselective Nitration of Olefins with ^tBuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2013), 15(13), 3384-3387, database is CAplus and MEDLINE.

Nitroolefins are essential elements for both synthetic chem. and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Dianati, Vahid published the artcileImproving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue, Application In Synthesis of 5153-73-1, the publication is Journal of Medicinal Chemistry (2018), 61(24), 11250-11260, database is CAplus and MEDLINE.

Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH₂ sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-DLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors.

Journal of Medicinal Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Application In Synthesis of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ieda, Naoya published the artcileDevelopment of photoredox-reaction-driven NO-releasing reagents and application for photomanipulation of vasodilation, Application In Synthesis of 26187-28-0, the publication is Yuki Gosei Kagaku Kyokaishi (2020), 78(11), 1048-1057, database is CAplus.

Nitric oxide (NO) is a signaling mol. that mediates vasodilation, neurotransmission, and immune response. Due to its instability in biol. environments, NO-releasing small-mol. compounds have been developed for biol. experiments and also as therapeutic reagents for vascular diseases. Although photocontrollable NO releasers are very useful chem. tools because of their precise operability in response to light irradiation, their biol. applications have been limited, mainly because they require UV light irradiation or contain metal ions with the potential to cause cytotoxicity. In order to overcome these problems, our group has developed visible-light-responsive NO releasers based on photoreodox reaction. These compounds are composed of two moieties, an NO-releasing moiety and a light-harvesting antenna moiety. After photoirradiation, photoinduced electron transfer from the NO releasing moiety to the antenna takes place, followed by NO release. Based on this system, we developed a blue-light-controllable NO releaser and a yellowish-green-light-controllable one, which are applicable for cellular and ex vivo experiments This account focuses on recent developments in photoredox-driven NO releasers and their applications for spatiotemporally controlled NO release in cells and ex vivo.

Yuki Gosei Kagaku Kyokaishi published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Application In Synthesis of 26187-28-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kiyokawa, Kensuke published the artcileStraightforward Synthesis of 1,2-Dicyanoalkanes from Nitroalkenes and Silyl Cyanide Mediated by Tetrabutylammonium Fluoride, Computed Properties of 5153-73-1, the publication is Chemistry – A European Journal (2015), 21(3), 1280-1285, database is CAplus and MEDLINE.

A straightforward synthesis of 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN [R = 4-OCH₃C₆H₄, thiophen-2-yl, pyridin-3-yl, etc.; R¹ = H; RR¹ = (CH₂)₄] by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride was described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride was essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol was applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes RCH(CN)CH(R¹)CN.

Chemistry – A European Journal published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kashanna, Jajula published the artcilePalladium catalyzed carboannulation of nitrostyrenes with internal alkynes: a new synthetic strategy for cross coupling/C-H annulation and facile access to indenones, Application In Synthesis of 5153-73-1, the publication is Tetrahedron Letters (2016), 57(14), 1576-1581, database is CAplus.

Palladium(II) catalyzed carboannulation reaction of internal alkynes with nitrostyrenes to afford 2,3-disubstituted indenones is reported. The annulation reaction proceeds through transmetalation of Pd(II) with aldehydes generated from the nitrostyrene (C-H activation) and insertion of the alkynes, followed by cyclization via intramol. nucleophilic addition of intermediate organopalladium(II) species. This reaction proceeded in moderate to good yields and with high regioselectivity. Electron-rich nitrostyrenes were transformed to the corresponding aldehydes in high yields without addition of any peroxide reagent.

Tetrahedron Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Application In Synthesis of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Caporali, Maria published the artcileNew diphosphine ligands based on diphenyl ether for the Pd-catalyzed CO/ethene copolymerization, SDS of cas: 68569-14-2, the publication is Chemical Communications (Cambridge, United Kingdom) (2005), 3478-3480, database is CAplus and MEDLINE.

The catalytic activity and selectivity of palladium(II) complexes of flexible phosphine bidentate ligands in the CO/ethene polymerization reaction change considerably with the steric effects of the ligands.

Chemical Communications (Cambridge, United Kingdom) published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, SDS of cas: 68569-14-2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Griffiths, M. H. published the artcileThe comparative metabolism of 2,6-dichlorothiobenzamide (Preflx) and 2,6-dichlorobenzonitrile in the dog and rat, Related Products of nitriles-buliding-blocks, the publication is Biochemical Journal (1966), 98(3), 770-81, database is CAplus and MEDLINE.

A single oral dose of either 2,6-dichlorothiobenzamide-¹⁴C (I) or 2,6-dichlorobenzonitrile-¹⁴C (II) fed to rats is almost entirely eliminated in 4 days; 84.8-100.5% of ¹⁴C from I is excreted 67.3-79.7% in the urine; 85.8-97.2% of ¹⁴C from II is excreted, 72.3-80.7% in the urine. Only 0.37% of the I dose and 0.25 ± 0.03% of the II dose are present in the carcass plus viscera after gut removal. Rats do not show sex differences in the pattern of elimination of the resp. metabolites of the two herbicides. The rates of elimination of ¹⁴C from the two compounds in the 24-hr. and 48-hr. urines are not different from one another. After oral administration to dogs, 85.9-106.1% of ¹⁴C from I is excreted, 66.6-80.9% in the urine, and 86.8-92.5% of ¹⁴C from II is excreted, 60.0-70.1% in the urine. Dogs do not show sex differences in the pattern of eliminating the metabolites of either I or II. Dogs and rats do not show species differences in the patterns of elimination of the two herbicides. I and II are completely metabolized; unchanged I and II are absent from the urine and feces, and from the carcasses when elimination is complete. In the hydrolyzed urine of rats dosed with either I or II, 2,6-dichloro-3-hydroxybenzonitrile accounts for approx. 42% of the ¹⁴C, a further 10-11% is accounted for by 2,6-dichlorobenzamide, 2,6-dichlorobenzoic acid, 2,6-dichloro-3- and -4-hydroxybenzoic acid and 2,6-dichloro-4-hydroxybenzonitrile collectively, and 25-30% by six polar constituents, of which two are S-containing amino acids. In the unhydrolyzed urines of rats dosed with either I or II, there are present free 2,6-dichloro-3- and -4-hydroxybenzonitrile, their glucuronide conjugates, ester glucuronides of the principal aromatic acids that are present in the hydrolyzed urines, and two S-containing metabolites analogous to mercapturic acids or premercapturic acids.

Biochemical Journal published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ooi, T. published the artcileZr(OBu^t)₄ as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes: development of a new asymmetric cyanohydrin synthesis, COA of Formula: C8H6ClNO, the publication is Tetrahedron (2001), 57(5), 867-873, database is CAplus.

Zr(OBu^t)₄ can serve as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation of aldehydes and also facilitate MPV type cyanide transfer to aldehyde carbonyls with com. available acetone cyanohydrin under mild conditions. Based on this finding, a new procedure for asym. cyanohydrin synthesis has been developed employing (4R,5R)-2,2-dimethyl-α,α,α’,α’-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL, I) as a chiral ligand. For instance, sequential treatment of a CH₂Cl₂ solution of I (1 equiv) with Zr(OBu^t)₄ (1 equiv) and acetone cyanohydrin (2 equiv) at room temperature for 1 h, and subsequent reaction with 3-phenylpropanal at -40° for 7.5 h resulted in formation of the corresponding cyanohydrin in 63% isolated yield with 85% ee. The scope and limitations of this method have been clarified with various aldehydes as substrates.

Tetrahedron published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, COA of Formula: C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Junek, Hans published the artcileSyntheses with nitriles, LIV. Reduction of oximinomalonitrile to aminomalonitrile using Raney catalysts, HPLC of Formula: 5098-14-6, the publication is Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie (1979), 34B(2), 280-2, database is CAplus.

An improved synthesis of aminomalononitrile H₂NCH(CN)₂ (I) by using Raney-catalyst for the reduction of HON:C(CN)₂ (II) at H₂-pressure of 4 atm and 20° was given. Due to the reactivity of II some new derivatives of oximinocyanoacetamide are obtained by O– and N-acylation. Condensation of III with benzilmonoxime gave 2-amino-5,6-diphenylpyrazinecarbonitrile; with N-phenylformamidate 2-amino-2,2-dicyano-1-(N-phenylimino)-acetaldehyde was obtained.

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, HPLC of Formula: 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts