Month: December 2022

Wang, Shi-Ben published the artcileSynthesis and evaluation of anticonvulsant and antidepressant activities of 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives, Application In Synthesis of 612-13-5, the publication is Medicinal Chemistry Research (2014), 23(10), 4619-4626, database is CAplus.

7-Alkyl-7H-tetrazolo[1,5-g]purines were synthesized, and their anticonvulsant and antidepressant activities were evaluated in a mouse model. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock test and a rotated test in mice, resp. Most of the compounds had anticonvulsant activity. Among the compounds studied, 7-(3-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (I) was the most potent compound with a median ED (ED₅₀) of 28.9 mg/kg and a protective index of 15.8, possessing better anticonvulsant activity and higher safety than carbamazepine. To explain the possible mechanism of anticonvulsant activity, I was tested in pentylenetetrazole-induced seizures, and the results suggest that I exerts anticonvulsant activity through a GABA-mediated mechanism. Forced swimming test showed that at 40 mg/kg, some of the compounds have significant antidepressant activity, the most active compound being 7-(2-chlorobenzyl)-7H-tetrazolo[1,5-g]purine decreasing immobility time by 56%.

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 C8H7NO4, Application In Synthesis of 612-13-5.

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

Liu, Da-Chuan published the artcileSynthesis and Anticonvulsant Activity Evaluation of 7-Alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones, Name: 2-(Chloromethyl)benzonitrile, the publication is Archiv der Pharmazie (Weinheim, Germany) (2014), 347(4), 268-275, database is CAplus and MEDLINE.

A new series of 7-alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones were synthesized and evaluated for their anticonvulsant activities. Among these compounds, 7-propoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one and 7-butoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one (I) showed the highest activity against maximal electroshock (MES)-induced tonic extension [(ED)₅₀ = 11.4 and 13.6 mg/kg, resp.]. It is worth mentioning that compound I showed especially low neurotoxicity, which led to a high protective index (PI >51). The orally anticonvulsant activity data of compound I further confirmed its efficacy, in an MES test, and its high safety with a PI value of 50.2. In addition, the potency of compound I against seizures induced by pentylenetetrazole, 3-mercaptopropionic acid, and bicuculline in the chem.-induced seizure tests suggested that compound I may exert its anticonvulsant activity through affecting the GABAergic system.

Archiv der Pharmazie (Weinheim, Germany) 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

Marco, Jose L. published the artcileSynthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca²⁺ channels and nicotinic receptors, HPLC of Formula: 5098-14-6, the publication is Bioorganic & Medicinal Chemistry (2004), 12(9), 2199-2218, database is CAplus and MEDLINE.

The synthesis and the biol. activity of heterocyclic derivatives as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca²⁺ channels and nicotinic receptors, are described. These mols. are tacrine analogs, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active mols. ranges from 10.0 to 76.9. Interestingly, the oxazolo-tacrine’ derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca²⁺ channels, and three of them blocked the non-L type of Ca²⁺ channels. Mol. modeling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme.

Bioorganic & Medicinal 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, HPLC of Formula: 5098-14-6.

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

Zhang, Huifang M. published the artcileAntiviral Activity of an Isatin Derivative via Induction of PERK-Nrf2-Mediated Suppression of Cap-Independent Translation, Synthetic Route of 612-13-5, the publication is ACS Chemical Biology (2014), 9(4), 1015-1024, database is CAplus and MEDLINE.

The authors report an isatin derivative 45 (ID45) against coxsackievirus B3 (CVB3) replication, which was synthesized based on a high-throughput screen of a unique natural product library. ID45 showed the most potent anti-CVB3 activity among the four synthesized compounds Treatment of cells with ID45 before or after infection significantly reduced viral particle formation, resulting in protection of cells from virus-induced apoptosis. In addition, ID45 treatment caused remarkable up-regulation of glucose-regulated protein 78 (GRP78), a hallmark of endoplasmic reticulum (ER) stress and an indicator of enhanced cell viability. In identifying the ER stress response pathway induced by ID45, the authors found that ID45 activated PKR-like ER protein kinase (PERK) but failed to up-regulate eIF2α phosphorylation. Instead ID45 activated transcription factor Nrf2 (NF-E2-related factor-2), which is evidenced by its nuclear translocation and upregulation of its downstream target genes NQO1 (NAD(P)H quinone-oxidoreductase 1) and GCLM (glutamate-cysteine ligase, modifier subunit). This observation was further verified by using siRNAs of GRP78 or Nrf2, which blocked both the translocation of Nrf2 and up-regulation of its target genes, leading to aggressive viral replication and enhanced cell apoptosis. Finally, the authors found that ID45-induced up-regulation of NQO1 protected eIF4GI, a eukaryotic cap-dependent translation initiation factor, from cleavage by CVB3 protease and degradation by proteasomes. Taken together, the authors’ findings established that a novel antiviral mechanism of isatin derivative ID45 inhibits CVB3 replication by promoting cell survival through a PERK/Nrf2-dependent ER stress pathway, which benefits host cap-dependent translation but suppresses CVB3 cap-independent translation.

ACS Chemical Biology 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 C15H14O3, Synthetic Route of 612-13-5.

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

Wen, Hui published the artcileA high-resolution method to assess cell multinucleation with cytoplasm-localized fluorescent probes, Quality Control of 26187-28-0, the publication is Analyst (Cambridge, United Kingdom) (2016), 141(13), 4010-4013, database is CAplus and MEDLINE.

Cell multinucleation is closely related to chromosomal instability. We report a simple, convenient method to assess cell multinucleation with cytoplasm-localized fluorescent probes (CLFP) which is superior to conventional nuclear staining methods. The CLFP method provides high-resolution images that enable the accurate calculation of the number of nuclear fragments.

Analyst (Cambridge, United Kingdom) 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 C27H39ClN2, Quality Control of 26187-28-0.

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

Barbier, Vincent published the artcileMorita-Baylis-Hillman Reactions with Nitroalkenes: A Case Study, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is European Journal of Organic Chemistry (2015), 2015(17), 3679-3688, database is CAplus.

The use of a highly reactive super-DMAP catalyst in Morita-Baylis-Hillman (MBH) reactions of nitroalkenes with Et glyoxylate, which result in excellent conversions and short reaction times with, importantly, very low catalyst loading is reported. An extensive study of this particular reaction is presented, which examines all mechanistic and exptl. details. Several critical points were hence uncovered that include the correlation between reaction efficiency and Lewis basicity of the catalyst; the double role played by the promoter, primarily as a nucleophilic activator towards the nitroalkene, and as a Bronsted base that triggers glyoxylate depolymerization More generally, the limitations in the choice of electrophiles that can engage efficiently in MBH-type transformations are rationalized by the competition between a productive pathway and a nitroalkene polymerization process. Other aspects of this transformation, used as a case study, are presented in the light of phys. organic chem.

European Journal of Organic 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

Carpenter, K. published the artcileHerbicidal activity of halo hydroxybenzonitriles, Name: 2,6-Dichloro-3-hydroxybenzonitrile, the publication is Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent (1964), 29(3), 644-54, database is CAplus.

The activity of 37 specified analogs of the new herbicide ioxynil (4-hydroxy-3,5-diiodobenzonitrile) are compared in greenhouse screening experiments Ioxynil, applied to the leaves of seedlings, kills weed species belonging to the Compositae, Cruciferae, Chenopodiaceae, Polygonaceae, and Caryophyllaceae families. Replacement of one or both of the I atoms in ioxynil by Cl or Br influences the herbicidal spectrum but not the general level of herbicidal activity. However, the number of halogens introduced and their positions in the nucleus are both critical, since the peak of activity occurs with dihalogenation in the 3 and 5 positions. Conversion of the nitrile group into either the amide or carboxyl group and changes in the position of the hydroxyl group are all detrimental to activity. Acetylation of the hydroxyl group results in no loss of activity, but methylation causes some reduction of the herbicidal activity.

Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent 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, Name: 2,6-Dichloro-3-hydroxybenzonitrile.

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

Carpenter, K. published the artcileHerbicidal activity of halogenohydroxybenzonitriles, SDS of cas: 3336-34-3, the publication is Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent (1964), 29(3), 644-54, database is CAplus.

The activities of analogs of ioxynil (4-hydroxy-3,5-diiodobenzonitrile) (I) were compared in greenhouse experiments I applied in amounts of 0.25 kg./ha. to the leaves of seedlings, kills weed spp. belonging to the Compositae, Cruciferae, Chenopodiaceae, Polygonaceae, and Caryophyllaceae families. Replacement of one or both of the iodine atoms in I by Cl or Br influences the herbicidal spectrum, but not the general level of herbicidal activity as determined in the greenhouse. However, the number of halogens introduced and their positions in the nucleus are both critical, since the peak of activity occurs with dihalogenation in the 3- and 5-positions. Conversion of the CN group into either a CONH₂ or COOH group and changes in the position of the OH group are all detrimental to activity. Acetylation of the OH group results in no loss of activity, but methylation causes some reduction in the herbicidal activity.

Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent 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, SDS of cas: 3336-34-3.

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

Khanna, Avinash published the artcileDesign, Synthesis, and Pharmacological Evaluation of Second Generation EZH2 Inhibitors with Long Residence Time, HPLC of Formula: 57663-05-5, the publication is ACS Medicinal Chemistry Letters (2020), 11(6), 1205-1212, database is CAplus and MEDLINE.

Histone methyltransferase EZH2, which is the catalytic subunit of the PRC2 complex, catalyzes the methylation of histone H3K27-a transcriptionally repressive post-translational modification (PTM). EZH2 is commonly mutated in hematol. malignancies and frequently overexpressed in solid tumors, where its expression level often correlates with poor prognosis. First generation EZH2 inhibitors are beginning to show clin. benefit, and we believe that a second generation EZH2 inhibitor could further build upon this foundation to fully realize the therapeutic potential of EZH2 inhibition. During our medicinal chem. campaign, we identified 4-thiomethyl pyridone as a key modification that led to significantly increased potency and prolonged residence time. Leveraging this finding, we optimized a series of EZH2 inhibitors, with enhanced antitumor activity and improved physiochem. properties, which have the potential to expand the clin. use of EZH2 inhibition.

ACS Medicinal Chemistry Letters published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C8H8N2OS, HPLC of Formula: 57663-05-5.

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

Krumova, Katerina published the artcileBodipy Dyes with Tunable Redox Potentials and Functional Groups for Further Tethering: Preparation, Electrochemical, and Spectroscopic Characterization, Name: 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, the publication is Journal of the American Chemical Society (2010), 132(49), 17560-17569, database is CAplus and MEDLINE.

The preparation, spectroscopic, and electrochem. characterization of a family of 16 new bodipy dyes with tunable redox potentials and versatile functional groups is reported. Electron-withdrawing or -donating groups (Et, H, Cl, or CN) at positions C2 and C6 enabled tuning the redox potentials within a ca. 0.7 eV window without significantly affecting either the HOMO-LUMO gap or the absorption and emission spectra. Hydroxymethyl or formyl groups at the meso (C8) position in turn provided a handle for covalent tethering to receptors and biomols. of interest, which dispenses with the more commonly used meso-aryl moiety as a means to tag mols. The dyes can thus be coupled to both electrophiles and nucleophiles. Importantly, it is shown that meso-formyl bodipy dyes are nonemissive and have significantly lower molar extinction coefficients compared to their meso-hydroxymethyl and meso-acetoxymethyl counterparts (which in turn are bright, with emission quantum yields in the range of 0.7-1). The nonemissive meso-formyl bodipy dyes thus provide unique opportunities as fluorogenic probes of nucleophilic attack and as fluorescent labeling agents where uncoupled fluorophores will not contribute to the fluorescence background. Overall, the new bodipy dyes reported here are promising candidates for the preparation of fluorescent sensors relying on photoinduced electron transfer and may find use in a number of fluorescent-labeling protocols.

Journal of the American Chemical Society 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, Name: 2,4-Dimethyl-1H-pyrrole-3-carbonitrile.

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