Tag: M.W=150-200

Kaesnaenen, Heikki published the artcile3-Heterocycle-Phenyl N-Alkylcarbamates as FAAH Inhibitors: Design, Synthesis and 3D-QSAR Studies, Product Details of C8H9NOS, the publication is ChemMedChem (2010), 5(2), 213-231, database is CAplus and MEDLINE.

Carbamates are a well-established class of fatty acid amide hydrolase (FAAH) inhibitors. Herein is described the synthesis of meta-substituted phenolic N-alkyl/aryl carbamates and their in vitro FAAH inhibitory activities. The most potent compound, 3-(oxazol-2-yl)phenyl cyclohexylcarbamate (I), inhibited FAAH with a sub-nanomolar IC₅₀ value (IC₅₀=0.74 nM). Addnl., three-dimensional quant. structure-activity relationships (QSAR) models of FAAH inhibition were developed and validated combining the newly disclosed carbamates with previously published inhibitors to give a total set of 99 compounds Prior to 3D-QSAR modeling, the degree of correlation between FAAH inhibition and in silico reactivity was also established. Both 3D-QSAR methods used, CoMSIA and GRID/GOLPE, produced statistically significant models with coefficient of correlation for external prediction (R²_PRED) values of 0.732 and 0.760, resp. These models could be of high value in further FAAH inhibitor design.

ChemMedChem published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Product Details of C8H9NOS.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Cherian, Joseph published the artcileStructure-Activity Relationship Studies of Mitogen Activated Protein Kinase Interacting Kinase (MNK) 1 and 2 and BCR-ABL1 Inhibitors Targeting Chronic Myeloid Leukemic Cells, Synthetic Route of 947533-21-3, the publication is Journal of Medicinal Chemistry (2016), 59(7), 3063-3078, database is CAplus and MEDLINE.

Clin. used BCR-ABL1 inhibitors for the treatment of chronic myeloid leukemia do not eliminate leukemic stem cells (LSC). It has been shown that MNK1 and 2 inhibitors prevent phosphorylation of eIF4E and eliminate the self-renewal capacity of LSCs. Herein, the authors describe the identification of novel dual MNK1 and 2 and BCR-ABL1 inhibitors, starting from the known kinase inhibitor. Initial structure-activity relationship studies resulted in a compound with loss of BCR-ABL1 inhibition. Further modification led to orally bioavailable dual MNK1 and 2 and BCR-ABL1 inhibitors I and II, which are efficacious in a mouse xenograft model and also reduce the level of phosphorylated eukaryotic translation initiation factor 4E in the tumor tissues. Kinase selectivity of these compounds is also presented.

Journal of Medicinal Chemistry published new progress about 947533-21-3. 947533-21-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Boronic acid and ester,Amine,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (6-Acetamidopyridin-3-yl)boronic acid, and the molecular formula is C7H9BN2O3, Synthetic Route of 947533-21-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Skorupska, Ewa A. published the artcileDynamic ¹H NMR spectroscopic study of hindered internal rotation in selected N,N-dialkyl isonicotinamides: an experimental and DFT analysis, Formula: C10H14N2O, the publication is Tetrahedron (2013), 69(38), 8147-8154, database is CAplus.

Dynamic ¹H NMR measurements were performed for N,N-dialkyl isonicotinamides (alkyl = Me, Et, and Me₂CH). Two complementary methods of the anal. of these spectra were used, targeting the estimation of rates of alkyl group exchange and thereby parameters for rotation around the C-N bond. The Gibbs free activation energy in DMSO, ΔG_exp^≠, is 67.6, 65.3, and 61.4 kJ mol^-1, resp. This finding was compared with related DFT and MP2 results on simulated solutions, ΔG_calcd^≠s, in search of the best theor. tool reflecting the observed trend that ΔG_exp^≠ reduces with an increasing bulkiness of the N-alkyl group. Especially, the DFT methods recommended for TS geometry and barrier height calculations were used. The barriers to C_ar-C(O) bond rotation were also computed, although not measured exptl. An IRC anal. was also carried out. As a result, the above trend was rationalized by steric hindrance in the ground-state forms under study. The changes in their geometric parameters, including pyramidicity descriptors, are fully consistent with such explanation. Among all DFT methods tested, only the use of the BB1K/6-31+G(d,p)/IEF-PCM(DMSO) protocol afforded ΔG_calcd^≠s fully comparable to the present DNMR determinations

Tetrahedron published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C12H14BNO2, Formula: C10H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Amaral, Miriam C. S. published the artcileCharacterization of residual organic compounds of aerobic degradation of landfill leachate, SDS of cas: 360-92-9, the publication is Journal of Environmental Science and Health, Part A: Toxic/Hazardous Substances & Environmental Engineering (2017), 52(7), 665-672, database is CAplus and MEDLINE.

The purpose of this article is to characterize and compare the residual COD of raw landfill leachate and its low and high mol. weight fractions before and after aerobic degradation process. The low and high mol. weight fractions (<10 kDa and >10 kDa, resp.) were obtained by the use of an ultrafiltration cell. Samples of the fractions with mol. weights 10 kDa, as well as the raw leachate, were characterized in terms of COD, protein, carbohydrate and lipid concentration and by biodegradability test. The compound identification of all samples was carried out using gas chromatog. coupled with mass spectrometry (GC/MS). The results show that the landfill leachate studied is constituted of approx. 60% of compounds with mol. weight <10 kDa. Approx. 80% of the compounds identified in the leachate had been degraded. This is an indication that most of the compounds that constitute the significant fraction of residual COD correspond to intermediate products and products of condensation of affluent compounds or had been generated during the degradation (SMP). Similar compounds were identified in all effluents of the degradation assay, suggesting the presence of SMP. These compounds, predominantly aliphatic and esters, are characterized by high mol. weight and probable refractory nature.

Journal of Environmental Science and Health, Part A: Toxic/Hazardous Substances & Environmental Engineering published new progress about 360-92-9. 360-92-9 belongs to amides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain,Amide, name is N,N-Diethyl-2,2,2-trifluoroacetamide, and the molecular formula is C6H10F3NO, SDS of cas: 360-92-9.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Koyama, Junko published the artcileStructure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds, HPLC of Formula: 530-40-5, the publication is Bioorganic & Medicinal Chemistry Letters (2005), 15(4), 1079-1082, database is CAplus and MEDLINE.

Antimicrobial activities of two azafluorenones, four 1-azaanthraquinones, five 2-azaanthraquinones, and one 2-azaquinone were tested. Several azaanthraquinones possessed broad, potent activity, while the azafluorenones demonstrated weak activity. The following structure-activity relationship was postulated: (1) activity decreased in the order 2-azaanthraquinones > 1-azaanthraquinones > azafluorenones; and (2) a hydroxyl group at the peri-carbonyl group enhanced activity. In addition, correlations among reduction potential, hydrophobic parameter, and antimicrobial activity were discussed.

Bioorganic & Medicinal Chemistry Letters published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, HPLC of Formula: 530-40-5.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Eccles, Kevin S. published the artcileCrystal Landscape of Primary Aromatic Thioamides, Safety of 3-Methoxybenzothioamide, the publication is Crystal Growth & Design (2014), 14(6), 2753-2762, database is CAplus.

The crystal landscape of primary aromatic thioamides is described, displaying similar characteristic intermol. H-bonding interactions in the solid state to those observed in their widely studied amide analogs, including R²₂(8) dimers and C(4) chains. In a number of cases, high Z’ values were observed in the structures. From the observed solid-state features, the thioamide functional group, which is a strong H-bond donor and moderate acceptor, offers considerable potential as a key moiety for crystal engineering. Crystallog. data and at. coordinates are given.

Crystal Growth & Design published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Safety of 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Amini, Ata published the artcileA Novel Logic-Based Approach for Quantitative Toxicology Prediction, SDS of cas: 2447-79-2, the publication is Journal of Chemical Information and Modeling (2007), 47(3), 998-1006, database is CAplus and MEDLINE.

There is a pressing need for accurate in silico methods to predict the toxicity of mols. that are being introduced into the environment or are being developed into new pharmaceuticals. Predictive toxicol. is in the realm of structure activity relationships (SAR), and many approaches have been used to derive such SAR. Previous work has shown that inductive logic programming (ILP) is a powerful approach that circumvents several major difficulties, such as mol. superposition, faced by some other SAR methods. The ILP approach reasons with chem. substructures within a relational framework and yields chem. understandable rules. Here, we report a general new approach, support vector inductive logic programming (SVILP), which extends the essentially qual. ILP-based SAR to quant. modeling. First, ILP is used to learn rules, the predictions of which are then used within a novel kernel to derive a support-vector generalization model. For a highly heterogeneous dataset of 576 mols. with known fathead minnow fish toxicity, the cross-validated correlation coefficients (R²_CV) from a chem. descriptor method (CHEM) and SVILP are 0.52 and 0.66, resp. The ILP, CHEM, and SVILP approaches correctly predict 55, 58, and 73%, resp., of toxic mols. In a set of 165 unseen mols., the R² values from the com. software TOPKAT and SVILP are 0.26 and 0.57, resp. In all calculations, SVILP showed significant improvements in comparison with the other methods. The SVILP approach has a major advantage in that it uses ILP automatically and consistently to derive rules, mostly novel, describing fragments that are toxicity alerts. The SVILP is a general machine-learning approach and has the potential of tackling many problems relevant to chemoinformatics including in silico drug design.

Journal of Chemical Information and Modeling published new progress about 2447-79-2. 2447-79-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Benzene,Amide, name is 2,4-Dichlorobenzamide, and the molecular formula is C7H5Cl2NO, SDS of cas: 2447-79-2.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Tenn, William J. III published the artcileAmidates as Leaving Groups: Structure/Reactivity Correlation of the Hydroxide-Dependent E1cB-like Breakdown of Carbinolamides in Aqueous Solution, COA of Formula: C7H5Cl2NO, the publication is Journal of Organic Chemistry (2007), 72(16), 6075-6083, database is CAplus and MEDLINE.

The kinetic study of the aqueous reaction, between pH 10 and 14, of eight N-(hydroxymethyl)benzamide derivatives in water at 25 °C, I = 1.0 M (KCl), was performed. In all cases, the reaction proceeds via a specific-base-catalyzed deprotonation of the hydroxyl group followed by rate-limiting breakdown of the alkoxide to form aldehyde and amidate (E1cB-like). Such a mechanism was supported by the lack of general buffer catalysis and the first-order dependence of the rate of reaction at low hydroxide concentrations and the transition to zero-order dependence on hydroxide at high concentration A ρ-value of 0.67 was found for the Hammett correlation between the maximum rate for the hydroxide independent breakdown of the deprotonated carbinolamide (k₁) and the substituent on the aromatic ring of the title compounds Conversely, the substituents on the aromatic ring of the amide portion of the carbinolamide had only a small effect on the K_a of the hydroxyl group indicating that the amide group does not strongly transmit the electronic information of the substituents. The major effect of electronic changes on the amide of carbinolamides is reflected in the nucleofugality of the amidate once the alkoxide is formed and not in the pK_a of the hydroxyl group of the carbinolamide.

Journal of Organic Chemistry published new progress about 2447-79-2. 2447-79-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Benzene,Amide, name is 2,4-Dichlorobenzamide, and the molecular formula is C22H12F6O6S2, COA of Formula: C7H5Cl2NO.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Sam, Joseph published the artcileHypotensive agents. Pyridinecarboxamides and piperidinecarboxamides, Related Products of amides-buliding-blocks, the publication is Journal of the American Chemical Society (1959), 710-13, database is CAplus.

Nicotinic acid (100 g.) in 2 l. CH₂Cl₂ treated gradually with 81 g. Et₃N, the mixture treated at 0-5° with 95 g. ClCO₂Et during 15-20 min., kept 0.5 hr. at 0°, treated with 57 g. pyrrolidine at 0-5°, warmed to room temperature, after 2 hrs. washed twice with 150 cc. H₂O, and distilled gave 90 g. 1-nicotinoylpyrrclidine, b_0.3 131-3°; methiodide m. 213.5-14.5° (MeCN), 87% yield. Similarly were prepared the following compounds (b.p./mm. and % yield given): N,N-diethylamide of isonicotinic acid (I), 109°/0.5 62; morpholide (II) of I, 142-5°/0.4, 55 [II.PhCH₂CH₂Br m. 214-15° (MeOH-Me₂CO), 97%]; morpholide (III) of nicotinic acid (IV), 190-5°/0.4, 48 [III.PhCH₂CH₂Br m. 212-13° (MeOH-Et₂O), 95%]; morpholide (V) of pyridine-2-carboxylic acid (VI), 142-3°/1, 59 [VI.MeI m. 175-6° (MeOH), 81%]; 2,6-dimethylmorpholide of IV, 138-40°/0.5, 57; 2,6-dimethylmorpholide (VII) of I, 135-7°/0.3, 50 [VII.PhCH₂CH₂Br m. 227-8° (MeOH-Et₂O), 94%]; 2,6-dimethylpiperidide of I, – (m. 73-4°), 20; 4-methylpiperazide of I, 133-5°/0.4, 39; p-ethoxyanilide (VIII) of IV, – (m. 170-5°), 50 [VIII.MeI m. 194-6°, 92%; VIII.PhCH₂CH₂Br m. 243-4° (MeOH), 88%]; p-dimethylaminoanilide (IX) of VI, -, 60 [IX.2HCl m. 227-30° (decomposition); IX.MeI m. 229-30° (decomposition)(MeOH), 98%]; p-dimethylaminoanilide (X) of IV, – (m. 185-7°), 25 [X.MeI m. 230-5° (decomposition)(MeOH), 95%]; p-dimethylaminoanilide (XI) of I, -, 38 [X.2HCl m. 175° (decomposition); X.MeI m. above 200° (decomposition)(MeOH), 90%]. The appropriate pyridinecarboxamide in MeOH or MeCN refluxed 24 hrs. with 10-20% suitable halide, the resulting quaternary salts in H₂O or EtOH hydrogenated over PtO₂ (0.3 g./0.1 mole) at 50-60 lb. during 15-30 hrs., filtered, basified strongly with 50% aqueous NaOH, extracted with Et₂O, and the extract worked up yielded the corresponding piperidinecarboxamide. N,N-Diethylnipecotamide (XII) (19 g.), 20 g. PhCH:CHCH₂Br, and 20 g. K₂CO₃ in 200 cc. PhMe refluxed 3 hrs. with stirring, cooled, washed with H₂O, dried, and distilled yielded 27 g. 1-cinnamyl derivative of XII, b_0.4 184-7°. Similarly were prepared the following 1-substituted piperidinecarboxamides (b.p./mm. and % yield given): 1-Ph(CH₂)₂ deriv, of XII, 173°/0.3, 86 (n²⁷_D 1.5221); 1-Ph₂CH derivative of XII.HBr, -, 20 [m. 234.5-35° (MeOH)]; 1-PhCH₂ derivative of the 4-isomer of XII, 173-5°/0.7, 87; 1-Me derivative of the pyrrolidide (XIII) of nipecotic acid (XIV), 111-14°/0.3, 89; 1-PhCH₂CH₂ derivative of XIII, 181-3°/0.1, 62 (n²⁵_D 1.5431); morpholide (XIV) of piperidine-2-carboxylic acid (XV), 143-5°/1.5, 65; 1-Me derivative of XIV, 121-3°/0.8, 87 (n³²_D 1.5013); 1-PhCH₂CH₂ derivative of XIV, 192-5°/0.4, 16 (n²⁴_D 1.5426); 1-Me derivative of the morpholide (XVI) of XIV, 118°/0.2, 72 (n^25.5_D 1.5065); 1-PhCH₂ derivative of XVI, 183-6°/0.3, 80; 1-PhCH₂CH₂ derivative of XVI, 188-92°/0.2, 85 (n³⁴_D 1.5406); 1-Ph(CH₂)₃ derivative of XVI, 203-6°/0.3, 71; 1-PhCH₂CH₂ derivative (XVII) of the morpholide of isonipecctic acid (XVIII), -, 85 [XVIII.HBr m. 279-80° (MeOH)]; 1-PhCH₂CH₂ derivative of the 2,6-dimethylmorpholide of XIV, 188-90°/0.2, 50 (n^24.5_D 1.5327); 1-PhCH₂CH₂ derivative (XIX) of the 2,6-dimethylmorpholide of XVIII, -, 78 [XIX.HBr m. 252-4° (H₂O)]; 1-Me derivative of the p-ethoxyanilide (XX) of XIV, -, 77 [m. 122-3° (aqueous MeOH)]: 1-PhCH₂CH₂ derivative (XXI) of XX, -, 82 [XXI.HBr m. 108-10° (decomposition) (Me₂CO)]; p-dimethylaminoanilide (XXII) of XV, -, 93 [m. 127-30° (aqueous MeOH)] [XXII.2HCl m. 248-50° (decomposition)(MeOH)]; p-dimethylaminoanilide (XXIII) of XVIII, [m. 197-8° (MeOH)], 90 [XXIII.2HCl m. 252-4° (decomposition) (MeOH)]. The appropriate 1-methylpiperidinecarboxamide reduced with LiAlH₄ yielded the corresponding alkylaminomethyl derivatives of 1-methylpiperidine (alkylamino group, b.p./mm., % yield, m.p., and % yield of dimethiodide given): 3-pyrrolidino, 59°/0.3, 93, 264-6° (decomposition), 94(at 25° in MeCN); 2-morpholino, 79-82°/0.4, 63, 255-6° (decomposition), 55 (refluxed 6 hrs. in MeCN); 3-morpholino, 87-8°/0.8 (n^25.5_D 1.5202), -, 281-2° (decomposition), – (refluxed 6 hrs. in MeOH). 1-Nicotinoylpyrrolidine in Et₂O reduced with LiAlH₄ yielded 44% 3-pyrrolidinomethylpyridine, b_0.2 75-7°, n^25.5_D 1.5202. XII (27.6 g.) and 18.2 g. styrene oxide heated 18 hrs. on the steam bath, the mixture dissolved in Et₂O and extracted with 6N HCl, the extract neutralized with NaOH and extracted with Et₂O, and the extract worked up gave 32.2 g. N,N-diethyl-1-(2-hydroxy-2-phenylethyl)nipecotamide, b_3.5 228-30°. XII (27.6 g.), 23.6 g. p-O₂NC₆H₄Cl, and 20.2 g. Et₃N heated 20 hrs. on the steam bath, cooled, triturated with H₂O, and filtered gave 45.1 g. N,N-diethyl-1-(p-nitrophenyl)nipecotamide (XXIV), m. 99.5-101.5° (EtOH). XXIV (15.3 g.) in 200 cc. EtOH hydrogenated at room temperature and 50 lb. over Raney Ni during 15 min., filtered, evaporated, the residue dissolved in Et₂O, and the solution saturated with dry Et₂O yielded 50% p-NH₂ analog di-HCl salt of XXIV, m. 227.5-8.5° (MeOH-EtOAc). 3-(3-Pyridyl)-acrylic acid (prepared in 79% yield from 3-pyridinecarboxaldehyde and malonic acid) treated in the usual manner with ClCO₂Et and morpholine in CH₂Cl₂ yielded 79% 4-[3-(3-pyridyl)acrylyl]morpholine (XXVI), m. 141-3° (MeCN). XXVI in MeOH hydrogenated at 60 lb. over 5% Pd-C yielded 87% 4-[3-(3-pyridyl)propionyl]morpholine (XXVII), b₁ 188-90°, n^24.5_D 1.5457. XXVII and excess PhCH₂CH₂Br in MeCN refluxed 18 hrs., the MeCN removed in vacuo, the residual oil dissolved in H₂O, the solution hydrogenated over PtO₂ at 60 lb. and 50°, and the mixture worked up in the usual manner yielded 84% 4-[3-(1-phenethyl-3-piperidyl)propionyl]morpholine, b_0.3 217-19°.

Journal of the American Chemical Society published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Cohen, Irit published the artcileSunlight assisted direct amide formation via a charge-transfer complex, Name: N,N-Diethylisonicotinamide, the publication is Chemical Communications (Cambridge, United Kingdom) (2017), 53(73), 10128-10131, database is CAplus and MEDLINE.

We report on the use of charge-transfer complexes between amines and carbon tetrachloride, as a novel way to activate the amine for photochem. reactions. This principle is demonstrated in a mild, transition metal free, visible light assisted, dealkylative amide formation from feedstock carboxylic acids and amines. The low absorption coefficient of the complex allows deep light penetration and thus scale(coating process) up to a gram scale.

Chemical Communications (Cambridge, United Kingdom) published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Name: N,N-Diethylisonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics