Category: 612-13-5

Lv, Zhiliang published the artcileDesign and synthesis of novel 2′-hydroxy group substituted 2-pyridone derivatives as anticancer agents, Computed Properties of 612-13-5, the publication is European Journal of Medicinal Chemistry (2013), 447-453, database is CAplus and MEDLINE.

The authors have synthesized a series of novel pyridones I [R = Ph, 2-BrC₆H₄, 4-ClC₆H₄, etc.] and evaluated their antitumor activities in vitro. The bioassays showed that the majority of the resultant compounds exerted inhibitory effects on six human cancer cell lines to various extents. Compound I [R = 4-ClC₆H₄] showed the best antitumor activities (IC₅₀ values of A549, HeLa and SW480 cancer cell lines were 0.86±0.17 μM, 0.54±0.23 μM and 0.21±0.13 μM, resp.).

European 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 C8H6ClN, Computed Properties of 612-13-5.

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

Jiang, Huanfeng published the artcileA Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO₂, and Chloroalkanes, Synthetic Route of 612-13-5, the publication is Organic Letters (2019), 21(2), 345-349, database is CAplus and MEDLINE.

Chloroalkyl and benzylic o-chlorobenzoates such as I were prepared by three-phase, four-component coupling reactions of o-trimethylsilylaryl triflates, KCl, CO₂, and dichloroalkanes such as 1,2-dichloroethane or benzylic chlorides, incorporating both chloride and CO₂ simultaneously. I underwent nucleophilic substitution reactions at the alkyl chloride moiety and a Suzuki coupling reaction at its aryl chloride moiety.

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, Synthetic Route of 612-13-5.

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

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

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

Chen, Wen-Xin published the artcileBase-promoted N-alkylation using formamides as the N-sources in neat water, Computed Properties of 612-13-5, the publication is Tetrahedron (2014), 70(4), 880-885, database is CAplus.

An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.

Tetrahedron 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, Computed Properties of 612-13-5.

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

Zhao, Xuelian published the artcileSynthesis and biological evaluation of isatin derivatives containing 1,3,4-thiadiazole as potent a-glucosidase inhibitors, Name: 2-(Chloromethyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 128447, database is CAplus and MEDLINE.

A series of isatin derivatives containing 1,3,4-thiadiazole derivatives I [R = 2-F, 3-CN, 4-Cl, etc.] were designed and synthesized. All newly synthesized compounds I were evaluated for their α-glucosidase inhibitory activity with resveratrol as pos. control in-vitro. Except for compounds I [R = 2-CN, 3-CN], all of the compounds I showed a potent inhibitory activity against α-glucosidase with IC₅₀ values in the range of 3.12 ± 1.25 to 45.95 ± 1.26μM and the purity of these compounds were greater than 95%. The IC₅₀ values were being compared to the standard resveratrol (IC₅₀ = 22.00 ± 1.15μM) and it was found that compounds I [R = H, 2-F, 2-Cl, 3-Cl, 4-Cl, 2-Br] were found to be more active than resveratrol. Specifically,I [R = 4-Cl] exhibited the most potent α-glucosidase inhibitory activity with IC₅₀ value of 3.12 ± 1.25μM. The kinetic anal. revealed that compound I [R = 4-Cl] was noncompetitive inhibitor. Structure activity relationship was established for all compounds I. Furthermore, the binding interactions of compound I [R = 4-Cl] with the active site of α-glucosidase were confirmed through mol. docking. This study was identified a new class of potent α-glucosidase inhibitors for further investigation.

Bioorganic & Medicinal Chemistry 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 C3H5F3O, Name: 2-(Chloromethyl)benzonitrile.

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

Chen, Xuwang published the artcileSynthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors, Application In Synthesis of 612-13-5, the publication is European Journal of Medicinal Chemistry (2012), 60-66, database is CAplus and MEDLINE.

A novel series of piperidine-substituted triazine derivatives I(Y = NHMe, MeO, R = 4-F, 4-NO₂, 4-MeO, 4-CN, 3-CN, 2-CN, H) and II(Y = NHMe, MeO, R = 4-NO₂, 4-CO₂H, 4-OH, H) have been synthesized and evaluated for anti-HIV activities in MT-4 cells. Most compounds displayed extremely promising activity against wild-type HIV-1 with EC₅₀ values in low nanomolar concentration, better than that of Nevirapine, Delavirdine, Zidovudine and Dideoxycitidine, and higher potency towards the resistant mutant strain K103N/Y181C than that of Nevirapine and Delavirdine. Selected compounds were also assayed against reverse transcriptase with lower IC₅₀ values than that of Nevirapine. The structure-activity relationship (SAR) of these novel structural congeners was also discussed.

European 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 C8H6ClN, Application In Synthesis of 612-13-5.

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

Chen, Wenmin published the artcileDesign, synthesis and biological evaluation of N₂,N₄-disubstituted-1,1,3-trioxo-2H,4H-pyrrolo[1,2-b][1,2,4,6]thiatriazine derivatives as HIV-1 NNRTIs, Name: 2-(Chloromethyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry (2013), 21(22), 7091-7100, database is CAplus and MEDLINE.

A series of N₂,N₄-disubstituted-1,1,3-trioxo-2H,4H-pyrrolo[1,2-b][1,2,4,6]thiatriazine derivatives (PTTDs, I, X = H, F, Cl, Br; R = PhCH₂, 2-cyanobenzyl, CH₂CN, allyl, etc.) was designed and synthesized by a facile route. The biol. assay results showed that the five most potent compounds displayed inhibitory activity against HIV-1 at low micromolar concentrations (EC₅₀ = 5.1-8.9 μM). Structure-activity relationship anal. indicated that N₂-(3-halogenated-benzyl) analogs were more potent than N₂-(unsubstituted-benzyl) analogs. The N₄-substitutions contributed to the antiviral activity in the following order: 2-/3-cyano substituted benzyl > 2-/3-halogenated benzyl > non-substituted benzyl > 4-halogenated benzyl. Docking studies revealed the binding conformation of these compounds and provided critical insights for the further development of PTTD analogs.

Bioorganic & 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 C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

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

Xu, Xin-Gang published the artcileHeat Capacity and Enthalpy of Formation of Trimethyl Phosphite, 2-Chloromethylbenzonitrile, and 2-Dimethylphosphonomethylbenzonitrile, Product Details of C8H6ClN, the publication is Journal of Chemical & Engineering Data (2007), 52(4), 1189-1194, database is CAplus.

The heat capacities, C_p, of tri-Me phosphite, 2-dimethylphosphonomethylbenzonitrile, and 2-chloromethylbenzonitrile were measured with an adiabatic calorimeter, and the standard enthalpies of formation, Δ_fH^o(298.15 K) (l or cr), for the three substances were calculated For this purpose, C_p(T) values of tri-Me phosphite and 2-dimethylphosphonomethylbenzonitrile are measured in the temperature range from (298.15 to 350.32) K, and the C_p(T) curves of 2-chloromethylbenzonitrile are also obtained for the crystal (300.35 to 329.00 K) and the liquid (337.26 to 372.45 K), resp. The deviation of exptl. heat capacities from the corresponding smoothed values lies within ± 1.5 %. A fusion transition phenomenon is found from the C_p(T) curves of 2-chloromethylbenzonitrile, and the enthalpy of fusion is measured with a differential scanning calorimeter (DSC). The gas-phase standard enthalpies of formation, Δ_fH^o(g, 298.15 K), of the three compounds are evaluated by the Benson group additive method. The critical temperature T_c, critical pressure P_c, and enthalpy of vaporization Δ_vapH^o of the compounds are also calculated by different group additive methods. On the basis of the above data, the values of Δ_fH^o(l, 298.15 K) of tri-Me phosphate and 2-dimethylphosphonomethylbenzonitrile and of Δ_fH^o(cr, 298.15 K) of 2-chloromethylbenzonitrile are estimated A thermochem. cycle including a chem. reaction is designed to examine the reliability of the values by measuring the heat of reaction. The result shows that the enthalpies of formation, Δ_fH^o(298.15 K) (l or cr), for the three substances are acceptable.

Journal of Chemical & Engineering Data 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 C4H6O3, Product Details of C8H6ClN.

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

Cao, Chao-Tun published the artcileDetermining the excited-state substituent constants σCCoex of ortho-substituents from 2,4′-disubstituted stilbenes, Synthetic Route of 612-13-5, the publication is Journal of Physical Organic Chemistry (2019), 32(8), n/a, database is CAplus.

There are mainly three kinds of substituent electronic effects derived from aromatic rings: ground-state, radical-state, and excited-state effect. However, excited-state substituent constants of ortho-substituents have not been reported up to now. In this paper, a method for extracting the excited-state substituent constant σCCoex of ortho-substituents was provided. Forty-nine 2,4′-disubstituted stilbenes were synthesized, and the UV absorption spectra of the synthesized stilbenes were determined The σCCoex values of ortho-substituents involving MeO, Me, F, Cl, Br, CF₃, and CN were quantified by curve fitting method based on the measured UV absorption spectra. The rationality of the σCCoexvalues were further exptl. confirmed by measuring the UV absorption spectra of other 10 samples of synthesized 2,3′-disubstituted stilbenes and by applying these σCCoexvalues in regression anal. of the UV absorption spectra for a complicated data set of 284 organic compounds

Journal of Physical Organic 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 C8H6ClN, Synthetic Route of 612-13-5.

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