Tag: M.W=150-200

Li, Shuan published the artcileSynthesis of hydralazine hydrochloride with by products in manufacture of o-cyanobenzyl chloride, Related Products of nitriles-buliding-blocks, the publication is Jingxi Shiyou Huagong (2008), 25(2), 32-35, database is CAplus.

A method for the synthesis of the title compound [i.e., hydralazine hydrochloride, 1-hydrazinylphthalazine hydrochloride (1:1)] is reported here. Hydralazine hydrochloride was synthesized from the byproducts, containing o-cyanotoluene, o-cyanobenzyl chloride and o-cyanobenzal chloride with the mass percentage of 10%, 30% and 50%, resp., generated from the manufacture of o-cyanobenzyl chloride. Effects of reaction temperature and time and ratio of reactants on the yield of o-cyanobenzaldehyde and hydralazine hydrochloride were investigated. The procedures and optimized conditions were found as follows: the byproduct reacted with chlorine at 150-155° in the presence of initiator, to give o-cyanobenzal chloride with purity of above 85%. Secondly, o-cyanobenzal chloride and sodium methoxide, in molar ratio of 1:2.05, were refluxed for 20 h to produce a corresponding acetal. Thirdly, that acetal was hydrolyzed with HCl, in n(acetal):n(HCl) = 1:3.9, at 0° for 3 h to obtain o-cyanobenzaldehyde (90.5% yield). Finally, hydralazine hydrochloride was synthesized (75% yield) by refluxing o-cyanobenzaldehyde and hydrazine for 8 h at a molar ratio of 1:3.5 in the presence of HCl and methanol.

Jingxi Shiyou Huagong 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, Related Products of nitriles-buliding-blocks.

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

He, Yu-Cai published the artcileBiocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401, Synthetic Route of 13312-84-0, the publication is Journal of Industrial Microbiology & Biotechnology (2010), 37(7), 741-750, database is CAplus and MEDLINE.

The nitrilase from Alcaligenes faecalis ECU0401 belongs to the category of arylacetonitrilase, which could hydrolyze 2-chloromandelonitrile, 3,4-dimethoxyphenylacetonitrile, mandelonitrile, and phenylacetonitrile into the corresponding arylacetic acids. To overcome the permeability barrier and prepare whole cell biocatalysts with high activities, permeabilization of Alcaligenes faecalis ECU0401 in relation to nitrilase activity was optimized by using cetyltrimethylammonium bromide (CTAB) as permeabilizing agent. The nitrilase activity from Alcaligenes faecalis ECU0401 increased 4.5-fold when the cells were permeabilized with 0.3% (w/v) CTAB for 20 min at 25°C and pH 6.5. Consequently, almost all the mandelonitrile was consumed and converted to (R)-(-)-mandelic acid with greater than 99.9% enantiomeric excess (e.e.) by the CTAB-permeabilized cells. The permeability barrier has been significantly reduced in the hydrolysis of mandelonitrile by using CTAB-permeabilized cells and a dynamic resolution was successfully achieved, giving a 100% theor. yield of (R)-(-)-mandelic acid. Efficient biocatalyst recycling was achieved as a result of cell immobilization in calcium alginate, with a product-to-biocatalyst ratio of 3.82 g (R)-(-)-mandelic acid g^-1 dry cell weight (dcw) cell after 20 cycles of repeated use.

Journal of Industrial Microbiology & Biotechnology 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, Synthetic Route of 13312-84-0.

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

Zhang, Chen-Sheng published the artcileEfficient production of (R)-o-chloromandelic acid by deracemization of o-chloromandelonitrile with a new nitrilase mined from Labrenzia aggregata, Category: nitriles-buliding-blocks, the publication is Applied Microbiology and Biotechnology (2012), 95(1), 91-99, database is CAplus and MEDLINE.

(R)-o-Chloromandelic acid (I) is the key precursor for the synthesis of Clopidogrel, a best-selling cardiovascular drug. Although nitrilases are often used as an efficient tool in the production of α-hydroxy acids, there is no practical nitrilase specifically developed for I. Here, a new nitrilase from L. aggregata (II) was discovered for the 1st time by genomic data mining, which hydrolyzed o-chloromandelonitrile (III) with high enantioselectivity, yielding (R)-o-chloromandelic acid in 96.5% ee. II was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties were studied. When III was used as the substrate, the V_max and K_m values of II were 2.53 μmol min^-1 mg^-1 protein and 0.39 mM, resp., indicating its high catalytic efficiency. In addition, a study of the substrate spectrum showed that II preferred to hydrolyze arylacetonitriles. To relieve substrate inhibition and to improve the productivity of II, a biphasic system of toluene-water (1:9, volume/volume) was adopted, in which III at 300 mM (apparent concentration, based on total volume) could be transformed by II in 8 h, giving an isolated yield of 94.5%. Thus, the development of II makes it possible to produce I by deracemizing III with a good ee value and high substrate concentration

Applied Microbiology and Biotechnology 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 C2H4ClNO, Category: nitriles-buliding-blocks.

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

Wang, Guan published the artcileDiscovery of a Novel Dual-Target Inhibitor of ERK1 and ERK5 That Induces Regulated Cell Death to Overcome Compensatory Mechanism in Specific Tumor Types, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Journal of Medicinal Chemistry (2020), 63(8), 3976-3995, database is CAplus and MEDLINE.

ERK1 and ERK5 are proposed to have pivotal roles in several types of cancer. Under some circumstance, ERK5 may provide a common bypass route, which rescues proliferation upon abrogation of ERK1 signaling. Thus, we accurately classified the tumor types from The Cancer Genome Atlas (TCGA) based on the expression levels of ERK1 and ERK5. We proposed a novel therapeutic strategy to overcome the above-mentioned compensatory mechanism in specific tumor types by co-targeting both ERK1 and ERK5. On the basis of the idea of overcoming ERK5 compensation mechanism, 22ac (ADTL-EI1712) as the first selective dual-target inhibitor of ERK1 and ERK5 was discovered to have potent antitumor effects in vitro and in vivo. Interestingly, this compound was found to induce regulated cell death accompanied by autophagy in MKN-74 cells. Taken together, our results warrant the potential of this dual-target inhibitor as a new candidate drug that conquers compensatory mechanism in certain tumor types.

Journal of Medicinal Chemistry 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 C6H12O2, Recommanded Product: 2-(Chloromethyl)benzonitrile.

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

Qiao, Jin-Bao published the artcileAllylboronates from Vinyl Triflates and α-Chloroboronates by Reductive Nickel Catalysis, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, the publication is Organic Letters (2020), 22(13), 5085-5089, database is CAplus and MEDLINE.

Allylboronates are unique building blocks widely used in organic synthesis, but the construction of cyclic allylboranates remains a challenging subject. The authors demonstrate here a mild and efficient access to this type of compound through the cross-electrophile coupling of vinyl triflates and α-chloroboronates. The reaction proceeded with a good substrate scope and good functional group compatibility. The ready availability of vinyl triflates from ketones, as well as the rich chem. of allylboranates, makes the authors’ method suitable for the divergent modification of biol. active compounds Preliminary mechanistic studies revealed that α-chloroboronates were activated via a radical process.

Organic Letters 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 C10H18BNO2, Recommanded Product: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile.

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

Zhang, Chun-Bo published the artcileDesign and synthesis of 6-alkyloxy[1,2,4]triazolo[1,5-a]quinazoline derivatives with anticonvulsant activity, Synthetic Route of 612-13-5, the publication is Medicinal Chemistry Research (2012), 21(10), 3294-3300, database is CAplus.

6-(Benzyloxy or alkoxy)[1,2,4]triazolo[1,5-a]quinazoline derivatives were synthesized in four steps starting from 1,3-cyclohexanedione, DMF-DMA, and aminotriazole followed by bromination, dehydrobromination and finally reaction with benzyl or alkyl halides. The anticonvulsant activity of all the target compounds, characterized by IR, ¹H-NMR and MS, were evaluated using Maximal electroshock test. The pharmacol. results showed that some of the compounds displayed pos. anticonvulsant activity. Among them, 6-(benzyloxy)-[1,2,4]triazolo[1,5-a]quinazoline was the most active compound with an ED₅₀ value of 78.9 mg/kg and a PI value of 9.0.

Medicinal Chemistry Research 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 C22H18Cl2N2, Synthetic Route of 612-13-5.

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

Zhang, Mengmeng published the artcileVisible Light Mediated C(sp³)-H Alkenylation of Cyclic Ethers Enabled by Aryl Ketone, Formula: C9H6N2O2, the publication is ChemCatChem (2019), 11(6), 1606-1609, database is CAplus.

C-H Alkenylation of cyclic ethers (THF, 1,4-dioxane) using the readily available nitroalkenes as the alkenylating reagents which gave α-alkenyl ethers Ar(CH:CH)_nR [Ar = Ph, 2-naphthyl, 2-thienyl, etc.; R = 1,2-dimethoxyethane, tetrahydrofuran-2-yl, 1,4-dioxan-2-yl] with high E-selectivity was developed. The mechanism study revealed that alkenylation proceeded through a proton coupled electron transfer (PCET) process with a de-nitration.

ChemCatChem 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 C8H16O2, Formula: C9H6N2O2.

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

Chen, Peiran published the artcileKinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Tetrahedron Letters (2014), 55(14), 2290-2294, database is CAplus.

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Tetrahedron 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, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Dou, Xiaowei published the artcileAsymmetric synthesis of 3-spirocyclopropyl-2-oxindoles via intramolecular trapping of chiral aza-ortho-xylylene, Category: nitriles-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(80), 9224-9226, database is CAplus and MEDLINE.

Chiral aza-ortho-xylylene intermediates were efficiently generated from 3-chloro-3-substituted oxindole precursors I (R = H, 5-Br, 6-Cl, 5-Cl) and (E)-R¹CH:CHNO₂ (R¹ = Ph, 2-BrC₆H₄, 3-BrC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 4-FC₆H₄, 2-MeC₆H₄, 4-MeOC₆H₄, 4-NCC₆H₄, 1-naphthyl, 2-furyl, 2-thienyl, phenethyl). The process was catalyzed by chiral quinine derivative II. The first intramol. trapping of chiral aza-ortho-xylylene intermediates led to a highly asym. synthesis of 3-spirocyclopropyl-2-oxindoles III.

Chemical Communications (Cambridge, United Kingdom) 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, Category: nitriles-buliding-blocks.

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

Han, Xiaoyu published the artcileA highly enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins mediated by a bifunctional quinine derived thiourea catalyst, COA of Formula: C9H6N2O2, the publication is Organic & Biomolecular Chemistry (2017), 15(16), 3401-3407, database is CAplus and MEDLINE.

A useful enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins catalyzed by a bifunctional quinine derived thiourea catalyst was developed. The Michael addition products could be obtained in good to high yields (68-92%) and with excellent enantioselectivities (89-98% ee). Such a reaction is exceptionally attractive in virtue of its simple protocol, ready availability of the starting materials, and practical applications of the products.

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, COA of Formula: C9H6N2O2.

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