Tag: M.W=150-200

Biswas, Soumen published the artcileDiastereoselective pot- and atom-economical synthesis of densely-substituted polycyclic 1,2- and 1,2,3-fused indole scaffolds, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Tetrahedron Letters (2019), 60(32), 150921, database is CAplus.

A simple, efficient, one-pot sequential process for the preparation of a family of 8,9-dihydropyrido[1,2-a]indol-6(7H)-one scaffolds I [R¹ = Ph, 2-ClC₆H₄, 2-furyl, etc.; stereo = cis, trans] in acceptable yields was established under mild conditions. The Michael-hemiaminalization-oxidation reaction proceeded between Me 2-(3-formyl-1H-indol-2-yl) acetate and trans-β-aryl/alkyl-substituted acroleins using pyrrolidine-BzOH as an efficient organocatalyst, followed by oxidation of in situ generated of C,N-fused hemiaminal adducts in the presence of PDC at room temperature Excitingly, organobase-catalyzed highly diastereoselective (up to ≤9:1 dr) construction of a series of pharmacol. attractive 1,2,3-fused tetracyclic indole scaffolds with five contiguous chiral centers including an all-carbon stereogenic center II [R² = CO₂Me, Ph, 2-furyl, etc.; R³ = Ph, 4-MeOC₆H₄] was achieved using developed method. Moreover, pyrrolidine-BzOH and PTSA as combined catalytic systems promoted the uninterrupted sequential Michael-cyclization reaction, followed by N-alkylation reaction with carbazole to produce interesting class of 6-(9H-carbazol-9-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indole derivatives III [R³ = Ph, 4-MeOC₆H₄] in a diastereoselective manner.

Tetrahedron 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, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Zhan, Peng published the artcileSynthesis and anti-HIV activity of novel 2,4-disubstituted-7-methyl-1,1,3-trioxo-2H,4H-pyrazolo[4,5-e][1,2,4]thiadiazine derivatives, Name: 2-(Chloromethyl)benzonitrile, the publication is Drug Discoveries & Therapeutics (2011), 5(6), 279-285, database is CAplus and MEDLINE.

Sixteen 2,4-dibenzyl-substituted 7-methyl-1,1,3-trioxo-2H,4H-pyrazolo[4,5-e][1,2,4]thiadiazines (PTDs) were prepared by a facile 1-pot reaction starting from 7-methyl-pyrazolo[4,5-e][1,2,4]thiadiazine and two different benzyl halides. The structures of all synthesized compounds were confirmed by ¹H- and ¹³C-NMR, IR spectra (IR) and mass spectra (MS). Anti-HIV activity was evaluated and none of the compounds inhibit HIV replication in human T-lymphocyte (MT-4) cell culture.

Drug Discoveries & Therapeutics 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 C9H9ClN2, Name: 2-(Chloromethyl)benzonitrile.

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

Liu, Xin-yong published the artcileSynthesis and anti-HIV activity evaluation of novel 2,4-disubstituted 7-methyl-1,1,3-trioxo-2,4-dihydro-pyrazolo-[4,5-e][1,2]thiadiazines, HPLC of Formula: 612-13-5, the publication is Archiv der Pharmazie (Weinheim, Germany) (2008), 341(4), 216-222, database is CAplus and MEDLINE.

A series of novel 2,4-disubstituted 7-methyl-1,1,3-trioxo-2,4-dihydro-pyrazolo[4,5-e] [1,2,4]thiadiazines (PTDs) was synthesized, structurally confirmed by spectral anal., and evaluated for their anti-HIV activities by inhibition of HIV-induced cytopathogenicity in MT-4 cell culture. The results showed that some compounds exhibited inhibitory activity specifically against HIV-2 replication. The most active HIV-2 inhibitor was compound I with an EC₅₀ value of 18.7 μM and SI = 15, which may provide a useful lead for further mol. optimization.

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, HPLC of Formula: 612-13-5.

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

Jin, Xin published the artcileDesign, synthesis, and anticancer activity of novel berberine derivatives prepared via CuAA C “click” chemistry as potential anticancer agents, Safety of 2-(Chloromethyl)benzonitrile, the publication is Drug Design, Development and Therapy (2014), 1047-1059, database is CAplus and MEDLINE.

A series of novel derivatives of phenyl-substituted berberine triazolyls has been designed and synthesized via copper-catalyzed azide-alkyne cycloaddition click chem. in an attempt to develop antitumor agents. All of the compounds were evaluated for anticancer activity against a panel of three human cancer cell lines, including MCF-7 (breast), SW-1990 (pancreatic), and SMMC-7721 (liver) and the noncancerous human umbilical vein endothelial cell (HUVEC) cell lines. The results indicated that most of the compounds displayed notable anticancer activities against the MCF-7 cells compared with berberine. Among these derivatives, compound 16 showed the most potent inhibitory activity against the SW-1990 and SMMC-7721 cell lines, with half-maximal inhibitory concentration (IC₅₀) values of 8.54±1.97 μM and 11.87±1.83 μM, resp. Compound 36 exhibited the most potent inhibitory activity against the MCF-7 cell line, with an IC₅₀ value of 12.57±1.96 μM. Compound 16 and compound 36 exhibited low cytotoxicity in the HUVEC cell line, with IC₅₀ values of 25.49±3.24 μM and 30.47±3.47 μM. Furthermore, compounds 14, 15, 16, 17, 18, 32, and 36 exhibited much better selectivity than berberine toward the normal cell line HUVEC.

Drug Design, Development and Therapy 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, Safety of 2-(Chloromethyl)benzonitrile.

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

Li, Guoshuai published the artcilePalladium-Catalyzed meta-Selective C-H Functionalization by Noncovalent H-Bonding Interaction, Recommanded Product: 2-Fluoro-4,5-dimethoxybenzonitrile, the publication is ACS Catalysis (2021), 11(16), 10460-10466, database is CAplus.

Herein, a palladium-catalyzed meta-selective C-H olefination of aromatic carbonyl compounds such as acetophenone, benzaldehyde, Me benzoate, N,N-diisopropylbenzamide, etc. by noncovalent hydrogen-bonding interaction was reported. N,N’-Substituted ureas RNHC(O)NHR¹ [R = cyclohexyl, 3,5-bis(trifluoromethyl)phenyl; R¹ = cyclohexyl, 2-(2-cyanophenoxy)ethyl, 2-phenoxyethyl, etc.] were engineered to serve as a H-bonding donor for binding to the substrates and, meanwhile, achieve site-selective control by the integrated directing group.

ACS Catalysis published new progress about 119396-88-2. 119396-88-2 belongs to nitriles-buliding-blocks, auxiliary class Fluoride,Nitrile,Benzene,Ether, name is 2-Fluoro-4,5-dimethoxybenzonitrile, and the molecular formula is C9H8FNO2, Recommanded Product: 2-Fluoro-4,5-dimethoxybenzonitrile.

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

Huang, Yunyuan published the artcileDiscovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects, Related Products of nitriles-buliding-blocks, the publication is European Journal of Medicinal Chemistry (2019), 111749, database is CAplus and MEDLINE.

Fructose-1,6-bisphosphatase (FBPase) is an essential enzyme of GNG pathway. Significant advances demonstrate the FBPase plays a critical role in treatment of diabetes. Numerous FBPase inhibitors were developed by targeting AMP site, nevertheless, none of these inhibitors has exhibited suitable potency and druggability. Herein, a new allosteric site (C128) on FBPase was discovered, and several nitrostyrene compounds exhibiting potent FBPase inhibitions were found covalently bind to C128 site on FBPase. Mutagenesis suggest that C128 is the only cysteine that can influence FBPase inhibition, the N125-S124-S123 pathway was most likely involved in allosteric signaling transmission between C128 and active site. However, these nitrostyrenes may bind with multiple cysteine besides C128 in FBPase. To improve pocket selectivity, a series of novel compounds (14a-14n) were re-designed rationally by integrating fragment-based covalent virtual screening and machine-learning-based synthetic complexity evaluation. As expected, the mass spectrometry validated that the proportion of title compounds binding to the C128 in FBPase was significantly higher than that of nitrostyrenes. Notably, under physiol. and pathol. conditions, the treatment of compounds 14b(I), 14c(II), 14i(III) or 14n(IV) led to potent inhibition of glucose production, as well as decreased triglyceride and total cholesterol levels in mouse primary hepatocytes. We highlight a novel paradigm that mol. targeting C128 site on FBPase can have potent hypoglycemic effect.

European Journal of Medicinal 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, Related Products of nitriles-buliding-blocks.

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

Jing, Ke published the artcileVisible-light photoredox-catalyzed carboxylation of benzyl halides with CO₂: Mild and transition-metal-free, Computed Properties of 612-13-5, the publication is Chinese Journal of Catalysis (2022), 43(7), 1667-1673, database is CAplus.

The visible-light photoredox-catalyzed carboxylation of benzyl chlorides and bromides with CO₂ has been reported. With inexpensive organic dyes as photocatalysts and amines as electron donors, this carboxylation proceeds well in the absence of sensitive organometallic reagents, transition metal catalysts, or metallic reductants. A wide range of com. available and inexpensive benzyl halides undergo such carboxylation to give valuable aryl acetic acids, including several pharmaceutical mols. and drug precursors, in moderate to high yields. Moreover, this reaction features mild reaction conditions (one atm. pressure of CO₂ and room temperature), broad substrate scope, good functional group tolerance, easy scalability, and low catalyst loading, thus providing an efficient approach for the assembly of aryl acetic acids.

Chinese Journal of Catalysis 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

Chen, Chen published the artcileDiastereo- and Enantioselective Synthesis of Functionalized Cyclopentenes Containing a Quaternary Chiral Center via a Thiosquaramide-Catalyzed Cascade Michael-Henry Reaction, HPLC of Formula: 5153-73-1, the publication is Journal of Organic Chemistry (2019), 84(23), 15655-15661, database is CAplus and MEDLINE.

An efficient method for the highly diastereoselective synthesis of chiral quaternary center-containing cyclopentenes via a cinchona alkaloid-derived thiosquaramide VIII-catalyzed tandem Michael-Henry reaction of phenacylmalononitriles and nitroolefins was developed. Meanwhile, up to 98% of enantioselectivity was observed A mechanism involving thiosquaramide-catalyzed asym. Michael addition and assisted E2 elimination was proposed based on exptl. data and preliminary theor. anal. (Hartree-Fock calculations).

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, HPLC of Formula: 5153-73-1.

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

Loudon, J. D. published the artcileElimination of sulfinate from sulfonic esters, HPLC of Formula: 13312-84-0, the publication is Journal of the Chemical Society (1959), 1780-2, database is CAplus.

In a typical experiment, 1.4 g. 2-ClC₆H₄CHO, 1.9 g. 4-MeC₆H₄SO₂Cl, 2 cc. dioxane, and 4 cc. H₂O, at 5° treated with 0.66 g. KCN, the mixture stirred 1 h., the solid filtered off, dissolved in 5 cc. 2:2:1 Me₂CO-EtOH-H₂O, filtered, and the filtrate treated with 3 g. ice gave 78% 2-ClC₆H₄CH(CN)OSO₂C₆H₄Me-4 (I), m. 86° (EtOH). In similar fashion were prepared the following RCH(CN)OSO₂C₆H₄Me-4 derivatives (R, % yield, and m.p. given): Ph(Ia), 72, 60°; 2-BrC₆H₄, 75, 104°; 3-MeOC₆H₄, 55, 52°: 2-O₂NC₆H₄(II), 72, 111°; 2,4-Cl₂C₆H₃, 72, 78°; 2,5-Cl(O₂N)C₆H₃, 70, 118°. PhCH(CN)OSO₂C₆H₃Cl₂-2,5, -, 102°, and 4-ClC₆H₄CH(CN)OSO₂C₆H₃Cl₂ -2,5, -, 86°, were also prepared II (1.66 g.) in 10 cc. EtOH kept 0.25 h. with 0.12 g. Na in 2 cc. EtOH, concentrated in vacuo, and the residual material extracted with C₆H₆ left 0.77 g. 4-MeC₆H₄SO₂Na(III) and the C₆H₆ solution chromatographed on alumina gave 0.68 g. O₂NC₆H₄CO₂Et (IV), m. 30°. All the above compounds gave good yields of the corresponding Na sulfinate. When the NaOEt in the experiment with I was replaced by NaCH(CO₂Et)₂, the products were III, IV, and 2-O₂NC₆H₄CH(CN)SO₂C₆H₄Me-4(V), m. 167°. I (1.5 g.) and 5 cc. Et₃N 0.5 h. at 100° gave 2-ClC₆H₄CH(CN)SO₂C₆H₄Me-4(VI), m. 112°, and 2-ClC₆H₄CO₂Et. PhSO₂NPh(CH₂Bz) (0.73 g.) in 10 cc. EtOH and 0.046 g. Na in 3 cc. EtOH as above gave III and BzCO₂Et (identified by reaction with ο-C₆H₄(NH₂)₂ as 2-phenylquinoxaline). Ia (2.87 g.), 20 cc. MeOH, and 1.53 g. NaBr refluxed 1 h. and concentrated gave 70% PhCH(CN)Br, b₁₅ 137-9°, m. 29°. I (0.32 g.), 0.13 g. 4-MeC₆H₄SH, and 0.04 g. NaOH in 8 cc. 4:1 EtOH-H₂O refluxed 0.5 h. gave 85% 2-ClC₆H₄CH(CN)SC₆H₄Me-4. I (0.32 g.) and 0.27 g. III in 5 cc. EtOH refluxed 48 h. gave VI. I (1.6 g.) and 2 cc. anhydrous C₅H₅N at 0° gave the pyridinium derivative (VII), m. 101° (C₆H₆-petr. ether); VII and 5N NaOH gave the betaine, dark red crystals, m. 138° (EtOH). I (0.32 g.) 3 cc. AcOH, 0.05 cc. concentrated H₂SO₄, and 0.15 g. 10% Pd on C absorbed 3 mol equivalents H in 3 h. to give 60% 2-ClC₆-H₄CH₂CH₂NH₂; picrate m. 186° (C₆H₆). CH₂N₂ (approx. 10 g.) in 50 mL. Et₂O and 15.5 g. PhCH₂COCl in 50 cc. Et₂O kept several hrs. and 17 g. powd. 4-MeC₆H₄SO₃H added gave after 12 h. at 20° PhCH₂COCH₂OSO₂C₆H₄Me-4, m. 63° (EtOH).

Journal of the Chemical Society 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, HPLC of Formula: 13312-84-0.

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

Mulder, A. H. published the artcileInhibitory action of 2,6-dichloro-3-hydroxybenzonitrile and 2,6-dichloro-4-hydroxybenzonitrile on the beating of heart cells in tissue culture. Antagonism of oligomycin, Synthetic Route of 3336-34-3, the publication is Biochimica et Biophysica Acta, Enzymology and Biological Oxidation (1966), 128(2), 391-3, database is CAplus.

The effects of 2,6-dichloro-3-hydroxybenzonitrile (I) and 2,6-dichloro-4-hydroxy-benzonitrile (II), uncouplers of oxidative phosphorylation, on the beating of heart cells were studied and compared with those obtained with 2,4-dinitrophenol (III). Concentrations of I, II, and III necessary to arrest beating were 0.3, 0.24, and 0.41 mM, resp. Oligomycin, when added 5 min. after these phenols had arrested the beating of the cells, partially restored the beating of I- or III-arrested cells, and completely restored the beating of II-arrested cells. ATP, to varying degrees, restored the beating of the phenol-arrested cells. III-treated cells started beating within 60 sec. after ATP addition, whereas I-treated cells began to beat 2-3 min. after ATP addition Cultures pretreated with II did not respond to ATP during the time of observation (6 min.). When II-inhibited cells were treated with oligomycin (20 γ/ml.) 6 min. after ATP addition, they started to beat again. A rise in frequency by ATP addition after oligomycin treatment was also observed on I-and III-inhibited cells. The differences in response to ATP additions by cells pretreated with these phenols probably reflect the quantitative differences in induction of ATPase in the living cells. The antagonism of oligomycin to the 2,6-dichlorobenzonitriles is in good agreement with the previous conclusion that the compounds act on the mitochondria and not on the cytoplasmic constituents of the living cell.

Biochimica et Biophysica Acta, Enzymology and Biological Oxidation 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, Synthetic Route of 3336-34-3.

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