Month: December 2022

Shi, Ce published the artcileDiscovery of Imidazoquinolines with Toll-Like Receptor 7/8 Independent Cytokine Induction, HPLC of Formula: 5098-14-6, the publication is ACS Medicinal Chemistry Letters (2012), 3(6), 501-504, database is CAplus and MEDLINE.

Toll-like receptors (TLRs) are key targets in the design of immunomodulating agents for use as vaccine adjuvants and anticancer treatments. The imidazoquinolines, imiquimod and resiquimod, have been shown to activate TLR-7 and -8, which in turn induce cytokine production as part of the innate immune response. Herein, we report the synthesis and discovery of a C7-methoxycarbonyl derivative of imiquimod (5, I) that stimulates cytokine production but is devoid of TLR-7/8 activity. Data are presented that shows that this analog not only induces IL-12p40 and TNF production, similar to that of imiquimod and resiquimod, but greatly enhances the production of IL-1β, a key cytokine involved in the activation of CD4 T cells. It is further demonstrated that TLR-7/8 activation can be recovered by the addition of a C2-alkyl substituent to this newly discovered analog. The results support the existence of an alternative mechanism of action by which imidazoquinolines can stimulate cytokine production

ACS Medicinal Chemistry Letters 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 C17H16O2, HPLC of Formula: 5098-14-6.

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

Li, Ninglin published the artcileCobalt-Catalyzed Protodeboronation of Aryl and Vinyl Boronates, Formula: C12H14BNO2, the publication is Journal of Organic Chemistry (2021), 86(2), 1972-1979, database is CAplus and MEDLINE.

An efficient cobalt-based catalytic system for protodeboronation of various aryl and vinyl boronates ArR [R = 5,5-dimethyl-1,3,2-dioxaborinan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl, 1,3,2-dioxaborolan-2-yl, 4-oxo-1,2,3,4-tetrahydro-1,3,2-benzodiazaborinin-2-yl; Ar = 4-chlorophenyl, 4-(9H-carbazol-9-yl)benzen-1-yl, anthracen-2-yl, etc.]/(E/Z)-Ar¹CH=C(R¹)R² (Ar¹ = 4-bromophenyl, 1-benzothiophen-2-yl, pyridin-2-yl, etc.; R¹ = H, Ph, tetramethyl-1,3,2-dioxaborolan-2-yl; R² = Ph, 5,5-dimethyl-1,3,2-dioxaborinan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl) is described. The reaction is capable of tolerating a wide range of functional groups. The reaction is also extended to deuterodeboronation with D₂O, which provides a potential protocol for the synthesis of regiospecifically deuterated arenes and olefins R³D [R³ = 4-phenylphenyl, 3-(4-cyanophenyl)prop-1-en-1-yl, 4-(9H-carbazol-9-yl)benzen-1-yl, 2-(4-([6,7-bis(2-methoxyethoxy)quinazolin-4-yl]amino)phenyl)ethenyl, etc.].

Journal of Organic Chemistry published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Formula: C12H14BNO2.

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

Lei, Zhen-lin published the artcileSynthesis with solvent-free and antifungal activities of 6-ether coumarin derivatives, Application In Synthesis of 612-13-5, the publication is Nongyao (2015), 54(10), 724-726, 743, database is CAplus.

2-Methyl-4-benzenediol was reacted with Et acetoacetate via Pechmann condensation to yield 6-hydroxy-4,7-dimethyl-coumarin, then the coumarin grinded with substituted benzyl chloride without solvent to yield twelve title compounds 4a-4l. The structure of the compounds were confirmed by ¹H NMR and LC-MS. The preliminary bioassay indicated some compounds, such as 4b, 4c and 4e, displayed over 90% antifungal activities against Botryodiplodia theobromae at 100 mg/L.

Nongyao 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, Application In Synthesis of 612-13-5.

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

Chen, Xiang-Yu published the artcileCatalytic MBH reaction of β-substituted nitroalkenes with azodicarboxylates, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic & Biomolecular Chemistry (2013), 11(34), 5722-5726, database is CAplus and MEDLINE.

An unprecedented N-heterocyclic carbene (NHC) catalyzed Morita-Baylis-Hillman (MBH) reaction of β-substituted nitroalkenes and azodicarboxylates has been developed. Both β-aryl and β-alkyl nitroalkenes worked well for the reaction using 5 mol% of NHC catalyst, giving the desired α-hydrazino-α,β-unsaturated nitroalkenes in good to excellent yields. E.g., in presence of NHC catalyst (I) and DMAP, Morita-Baylis-Hillman reaction of (E)-PhCH:CHNO₂ and DEAD gave 91% II.

Organic & Biomolecular 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, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Duong, Hung A. published the artcileCobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides, Application of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, the publication is Organometallics (2017), 36(22), 4363-4366, database is CAplus.

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

Organometallics published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Application of 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile.

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

Li, Xiangmin published the artcileOne-Pot Synthesis of Deuterated Aldehydes from Arylmethyl Halides, Application of 2-(Chloromethyl)benzonitrile, the publication is Organic Letters (2018), 20(7), 1712-1715, database is CAplus and MEDLINE.

A facile, one-pot approach for synthesizing deuterated aldehydes from arylmethyl halides was developed using D₂O as the deuterium source. The efficient process is realized by a sequence of formation, H/D exchange and oxidation of pyridinium salt intermediates. The mild and air-compatible reaction conditions enable efficient synthesis of diverse deuterated aldehydes with high deuterium incorporation.

Organic Letters 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, Application of 2-(Chloromethyl)benzonitrile.

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

Yang, Bowen published the artcileDiscovery of a series of 1H-pyrrolo[2,3-b]pyridine compounds as potent TNIK inhibitors, HPLC of Formula: 1036991-35-1, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 127749, database is CAplus and MEDLINE.

In an inhouse screening, 1H-pyrrolo[2,3-b]pyridine scaffold was found to have high inhibition on TNIK. Several series of compounds were designed and synthesized, among which some compounds had potent TNIK inhibition with IC₅₀ values lower than 1 nM. Some compounds showed concentration-dependent characteristics of IL-2 inhibition. These results provided new applications of TNIK inhibitors and new prospects of TNIK as a drug target.

Bioorganic & Medicinal Chemistry Letters published new progress about 1036991-35-1. 1036991-35-1 belongs to nitriles-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 3-Amino-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, and the molecular formula is C14H12N2S, HPLC of Formula: 1036991-35-1.

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

Li, Zhi published the artcileSeparation of chiral cyanohydrin enantiomers by gas chromatography, Application In Synthesis of 13312-84-0, the publication is Fenxi Huaxue (1997), 25(6), 708-713, database is CAplus.

The enantiomers of 14 cyanohydrins were separated on permethylated β-cyclodextrin column (fused silica, 25 m × 0.22 mm) by derivatization. The acetyl chloride and trifluoroacetic anhydride were used as derivatization reagents. All racemates were separated to baseline with separation factors (α) = 1.02-1.13. The enantiomer excess values of some enantiomers from asym. synthesis samples were determined, and they were identical with those by optical purity and HPLC methods. The separation effect of the two derivatization methods and the separation mechanism of enantiomers are discussed.

Fenxi Huaxue 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, Application In Synthesis of 13312-84-0.

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

Li, Ying published the artcileSynthesis and cytotoxicity of dihydroartemisinin ethers containing cyanoarylmethyl group, COA of Formula: C8H6ClNO, the publication is Bioorganic & Medicinal Chemistry (2003), 11(6), 977-984, database is CAplus and MEDLINE.

A new type of ether of dihydroartemisinin containing cyano and aryl groups was prepared and tested for cytotoxicity to A549, P388, L1210 and HT29 cells using the MTT assay. Compounds 12k and 12l were the most cytotoxic compounds Compound 13, lacking the peroxy group, showed a 1000-fold less potency than 12l. Similarly, the inactive compound 14 indicated that the position of cyano groups was also important. Flow cytometry data showed that the compounds caused an accumulation of P388 cells in the G₁-phase of the cell cycle.

Bioorganic & Medicinal Chemistry 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

Wang, Hui published the artcileSelective Coupling of 1,2-Bis-Boronic Esters at the more Substituted Site through Visible-Light Activation of Electron Donor-Acceptor Complexes, COA of Formula: C10H18BNO2, the publication is Angewandte Chemie, International Edition (2022), 61(18), e202202061, database is CAplus and MEDLINE.

1,2-Bis-boronic esters are useful synthetic intermediates particularly as the two boronic esters can be selectively functionalized. Usually, the less hindered primary boronic ester reacts, but herein, we report a coupling reaction that enables the reversal of this selectivity. This is achieved through the formation of a boronate complex with an electron-rich aryllithium which, in the presence of an electron-deficient aryl nitrile, leads to the formation of an electron donor-acceptor complex. Following visible-light photoinduced electron transfer, a primary radical is generated which isomerizes to the more stable secondary radical before radical-radical coupling with the arene radical-anion, giving β-aryl primary boronic ester products. The reactions proceed under catalyst-free conditions. This method also allows stereodivergent coupling of cyclic cis-1,2-bis-boronic esters to provide trans-substituted products, complementing the selectivity observed in the Suzuki-Miyaura reaction.

Angewandte Chemie, International Edition published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C14H31NO2, COA of Formula: C10H18BNO2.

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