Month: December 2022

Kelley, James L. published the artcile9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity, Related Products of nitriles-buliding-blocks, the publication is Journal of Medicinal Chemistry (1988), 31(10), 2001-4, database is CAplus and MEDLINE.

A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chloro substituent resulted in a substantial increase in antiviral activity. One of the most active compounds, 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine (I, R = Me), had an IC₅₀ value of 0.08 μM against serotype 1B. I (R = Cl, Me, Et, Me₂CH) were tested against 18 other rhinovirus serotypes, but the majority tested were less sensitive than type 1B. The range of serotype sensitivity for I (R = Me) varied from 0.08 to 14 μM. These 9-benzyl-2-chloro-9H-purines represent a new class of antiviral agents with in vitro activity against rhinoviruses.

Journal of Medicinal Chemistry published new progress about 115204-76-7. 115204-76-7 belongs to nitriles-buliding-blocks, auxiliary class 5.6_Aromatics,Purines, name is 4-((2,6-Dichloro-9H-purin-9-yl)methyl)benzonitrile, and the molecular formula is C13H7Cl2N5, Related Products of nitriles-buliding-blocks.

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

Luo, Wenqiang published the artcileChiral phosphoric acid catalyzed 1,3-dipolar cycloadditions of aldehydes, diethyl α-aminomalonate, and nitroalkenes, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron: Asymmetry (2014), 25(10-11), 787-791, database is CAplus.

A one-pot three component 1,3-dipolar cycloaddition reaction of an aldehyde, α-aminomalonate, and nitroalkene has been developed through a BINOL-derived chiral phosphoric acids. This reaction represents one of the most enantioselective catalytic approaches to access structurally diverse pyrrolidine derivatives Under optimized conditions the synthesis of the target compounds was achieved using (11bR)-2,6-bis(9-anthracenyl)-4-(hydroxy)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin (binaphthalenediol-derived cyclic phosphate) as catalyst.

Tetrahedron: Asymmetry 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, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Li, Yuanxiang published the artcileSynthesis and herbicidal activities of 2-[3-(2-substituted phenyl)-1H-pyrazol-1-yl]-4,6-dimethoxypyrimidine derivatives, COA of Formula: C8H6ClN, the publication is Youji Huaxue (2011), 31(3), 306-311, database is CAplus.

Twenty two novel 2-[3-(2-substitutedphenyl)-1H-pyrazol-1-yl]-4,6-dimethoxypyrimidine derivatives have been designed and synthesized using 1-(2-hydroxyphenyl)ethanone as starting material. All synthesized compounds were confirmed by ¹H NMR, MS techniques and elemental anal. The preliminary bioassay showed that some of them exhibited certain herbicidal activities.

Youji Huaxue published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, COA of Formula: C8H6ClN.

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

Thomas, K. R. Justin published the artcileLight-Emitting Carbazole Derivatives: Potential Electroluminescent Materials, Recommanded Product: 4-(3,6-Dibromo-9H-carbazol-9-yl)benzonitrile, the publication is Journal of the American Chemical Society (2001), 123(38), 9404-9411, database is CAplus and MEDLINE.

Stable carbazole derivatives that contain peripheral diarylamines at the 3- and 6-positions and an Et or aryl substituent at the 9-position of the carbazole moiety have been synthesized via palladium-catalyzed C-N bond formation. These new carbazole compounds (carbs) are amorphous with high glass transition temperatures (T_g, 120-194 °C) and high thermal decomposition temperatures (T_d > 450 °C). The compounds are weakly to moderately luminescent in nature. The emission wavelength ranges from green to blue and is dependent on the substituent at the peripheral nitrogen atoms. Two types of light-emitting diodes were constructed from carb: (I) ITO/carb/TPBI/Mg:Ag and (II) ITO/carb/Alq₃/Mg:Ag, where TPBI and Alq₃ are 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene and tris(8-hydroxyquinoline) aluminum, resp. In type I devices, the carb functions as the hole-transporting as well as emitting material. In type II devices, either carb, or Alq₃ is the light-emitting material. Several green light-emitting devices exhibit exceptional maximum brightness, and the phys. performance appears to be better than those of typical green light-emitting devices of the structure ITO/diamine/Alq₃/Mg:Ag. The relation between the LUMO of the carb and the performance of the light-emitting diode is discussed.

Journal of the American Chemical Society published new progress about 373389-97-0. 373389-97-0 belongs to nitriles-buliding-blocks, auxiliary class OLED Materials,Red Fluorescence Dopants, name is 4-(3,6-Dibromo-9H-carbazol-9-yl)benzonitrile, and the molecular formula is C16H14O6, Recommanded Product: 4-(3,6-Dibromo-9H-carbazol-9-yl)benzonitrile.

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

Hosmane, Ramachandra S. published the artcileRearrangements in heterocyclic synthesis: a novel translocation of an (N-amino-N-methylamino)methylene group from a heterocyclic N-amino-N-methylformamidine side chain to the vinylogous nitrile function, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Organic Chemistry (1988), 53(2), 382-6, database is CAplus.

Reaction of imidazole I (R = OMe) (II) with 1 equiv of N₂H₄ gave 1-amino-9-benzyl-6-iminopurine (III), which upon treatment with excess N₂H₄, rearranged to 9-benzyl-6-hydrazinopurine (IV). Reaction of II with MeNHNH₂ gave I (R = H₂NNMe) (V). Thermolysis of V in refluxing PhMe-MeOH containing CF₃CO₂H gave an equimolar mixture of 5-amino-1-benzyl-4-cyanoimidazole (VI) and triazole VII. VI was recycled to V via II. The structure of VII was established by spectral data and an unequivocal synthesis. The conversion of V to VII represents a novel translocative rearrangement involving the transfer of an H₂NNMeCH: group from the imidazole 5-position to the nitrile function at C-4. The rearrangement also occurs in the analogous pyrazole system.

Journal of Organic 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, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Monguzzi, R. published the artcileSynthesis of new α-hydrazinoarylacetic acids and derivatives, Related Products of nitriles-buliding-blocks, the publication is Farmaco, Edizione Scientifica (1976), 31(8), 549-60, database is CAplus and MEDLINE.

α-Hydrazinoarylacetic acids, e.g., PhCH(NMeNH2)CO2H, were prepared by reaction of α-bromoarylacetic acids with N2H4, alkylhydrazines and carbobenzyloxyhydrazines. Na-Hg reduction of α-hydrazono-2-thienylacetic acid and of α-hydrazono-(2,5-dichloro-3-thienyl)acetic acid gave α-hydrazino-2-thienylacetic acid and α-hydrazino-(2-chloro-4-thienyl)acetic acid. PhCHBrCO2H and PhCH2O2CNHNH2 gave PhCH(NHNHCO2CH2Ph)CO2H, which with 2,4-(O2N)2C6H3OH and dicyclohexylcarbodiimide gave 16% I (R = PhCH2O2C) (and smaller amounts of II), which was hydrogenolyzed with Pd/C to 53% I (R = H).

Farmaco, Edizione Scientifica published new progress about 49540-34-3. 49540-34-3 belongs to nitriles-buliding-blocks, auxiliary class Aliphatic Chain, name is Ethylhydrazine dihydrochloride, and the molecular formula is C2H10Cl2N2, Related Products of nitriles-buliding-blocks.

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

Chen, Wen-Hsuan published the artcileOne-Step Aminomalononitrile-Based Coatings Containing Zwitterionic Copolymers for the Reduction of Biofouling and the Foreign Body Response, Category: nitriles-buliding-blocks, the publication is ACS Biomaterials Science & Engineering (2019), 5(12), 6454-6462, database is CAplus and MEDLINE.

Many biomedical devices benefit from antibiofouling coatings, which can reduce biointerfacial interactions such as protein adsorption and cell attachment. In this study, we synthesized zwitterionic copolymers consisting of sulfobetaine methacrylate (SB) and 2-aminoethyl methacrylate (AE) via free radical polymerization and combined these copolymers in solution with aminomalononitrile to form zwitterionic coatings in an autopolymn. process. The successful deposition of coatings containing different SB/AE ratios was demonstrated by XPS. The one-step surface modification process was carried out on polydimethylsiloxane (PDMS), tissue culture polystyrene, and gold substrates, demonstrating that this method can be transferred to different substrate materials. The ability of optimized coatings to reduce serum protein adsorption was demonstrated by quartz crystal microbalance measurements while the ability to resist cell attachment for 24 h was demonstrated using L929 mouse fibroblasts. The stability of the coatings under physiol. conditions was investigated, and resistance to cell attachment was maintained over a period of 45 days. Furthermore, the resistance of the copolymer coating to cell attachment was maintained after both ethylene oxide sterilization and autoclaving. Finally, copolymer-modified PDMS samples were investigated with regard to their ability to reduce the foreign body response in vivo. Here, a significant reduction in the capsule thickness (approx. 50%) was observed in nude mice after 2 and 4 wk. It is expected that the one-step, facile, and versatile surface modification strategy discussed here will find applications in biomedical devices.

ACS Biomaterials Science & Engineering 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, Category: nitriles-buliding-blocks.

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

Liu, Yan-Kai published the artcileOpen-Close: An Alternative Strategy to α-Functionalization of Lactone via Enamine Catalysis in One Pot under Mild Conditions, Formula: C9H6N2O2, the publication is Organic Letters (2015), 17(8), 2022-2025, database is CAplus and MEDLINE.

An open-close strategy in asym. catalysis is newly developed. With this powerful strategy, lactols are directly applied as potential precursors of lactones in enamine-based asym. Michael reactions providing a facile access to α-functionalized lactones containing two adjacent stereogenic centers as a single diastereomer, e.g. I, in good to excellent yields (up to 99%) and with excellent enantioselectivities (most cases >99%). Moreover, the reaction products are shown to give highly functionalized derivatives by stepwise systematic transformations.

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, Formula: C9H6N2O2.

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

Liu, Tang-Lin published the artcileCyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(4), 651-654, database is CAplus and MEDLINE.

In the presence of Ti(Oi-Pr)₄, aldehyde and ketone cyanohydrins underwent amination reactions with amines such as 4-methoxyaniline to yield α-aminonitriles. Aryl, aryl alkyl, and dialkyl ketones and aryl and alkyl aldehyde cyanohydrins underwent amination. Reaction of aldehyde cyanohydrins with 4-methoxyaniline in the presence of Ti(Oi-Pr)₄, (S)-BINOL, and quinine yielded nonracemic (S)-α-aminonitriles in 31-88% ee. The reaction mechanism was studied; the reaction is proposed to occur by elimination of cyanide from the cyanohydrin followed by imine formation and addition of cyanide to the imine (“cyanide borrowing”) rather than by loss of a proton, imine formation, and reduction (“hydrogen borrowing”).

Chemical Communications (Cambridge, United Kingdom) 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, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Li, Qing-Hua published the artcileTitanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia, Formula: C8H6ClNO, the publication is Organic Letters (2019), 21(20), 8429-8433, database is CAplus and MEDLINE.

Herein, the direct amination of cyanohydrins with the partner of ammonia for the synthesis of N-unprotected α-aminonitriles H₂NC(R¹)(R²)CN (R¹ = Ph, 4-FC₆H₄, 2-thienyl, etc.; R² = H, Me, Et; -R¹R²– = -(CH₂)₄-) is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesized with moderate to high yields under mild reaction conditions.

Organic Letters 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, Formula: C8H6ClNO.

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