Month: January 2023

A carbon-13 NMR study of 5-cyano-, 5-methoxycarbonyl-, 5-carbamoyl-, and 5-acetyl-3-nitro-2-X-thiophenes: substituent effects and their relation to the charge distribution in corresponding 2,2-dimethoxy Meisenheimer adducts was written by Dell’Erba, Carlo;Sancassan, Fernando;Novi, Marino;Spinelli, Domenico;Consiglio, Giovanni;Arnone, Caterina;Ferroni, Fiammetta. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1989.Synthetic Route of C5H2N2O2S This article mentions the following:

A ¹³C NMR study in (CD₃)₂SO has been carried out on 5-cyano- (I), 5-methoxycarbonyl- (II), 5-carbamoyl- (III), and 5-acetyl-3-nitro-2-X-thiophenes (IV) in order to investigate the 2-X-substituent effect on the C(α) chem. shifts of the different 5-probes. The results obtained show that, unlike the case of the acetyl group, the α-carbon chem. shifts of the cyano, methoxycarbonyl, and carbamoyl groups are not appreciably affected by through-conjugation with the 2-X-substituents, π-polarization being the more important outcome of the substituent effect on the probe group. The anal. of both the C(5) and C(α) chem.-shift variations in I–IV by a gradual modification of the electron-releasing power of the substituents reveals a trend which has been interpreted as a useful indicator of the electronic effects in play on the distribution of the π-electron densities in the corresponding Meisenheimer adducts V (R = CN, CO₂Me, CONH, Ac). In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Synthetic Route of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Synthetic Route of C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amino-functionalized Zr(IV) metal-organic framework as bifunctional acid-base catalyst for Knoevenagel condensation was written by Yang, Yang;Yao, Hong-Fei;Xi, Fu-Gui;Gao, En-Qing. And the article was included in Journal of Molecular Catalysis A: Chemical in 2014.SDS of cas: 55490-87-4 This article mentions the following:

The amino-functionalized metal-organic framework of Zr(IV) with 2-aminoterephthalate, UiO-66-NH₂, was studied as a solid catalyst for Knoevenagel condensation. The material can efficiently catalyze the condensation reaction of benzaldehyde with Et cyanoacetate or malononitrile in highly polar solvents such as DMF, DMSO and ethanol. The catalytic system has also been tested for various aromatic aldehydes, the conversion easily reaching more than 90% under mild conditions. It was demonstrated that the catalytic process is heterogeneous and shows size effects, characteristic of a porous catalyst. The catalyst can be recycled without losing its framework integrity and catalytic activity. The catalytic activity has been compared with di-Me 2-aminoterephthalate and the isostructural amino-free MOF (UiO-66). The superior performance of UiO-66-NH₂ has been attributed to the site-isolated acid-base bifunctional character. It has been proposed that the Zr site in close proximity to the amino group activates aldehydes to promote the formation of aldimine intermediates from the aldehydes and the amino group. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4SDS of cas: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.SDS of cas: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6-Cyclohexylmethyl-3-hydroxypyrimidine-2,4-dione as an inhibitor scaffold of HIV reverse transcriptase: Impacts of the 3-OH on inhibiting RNase H and polymerase was written by Tang, Jing;Kirby, Karen A.;Huber, Andrew D.;Casey, Mary C.;Ji, Juan;Wilson, Daniel J.;Sarafianos, Stefan G.;Wang, Zhengqiang. And the article was included in European Journal of Medicinal Chemistry in 2017.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

3-Hydroxypyrimidine-2,4-dione (HPD) represents a versatile chem. core in the design of inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H and integrase strand transfer (INST). We report herein the design, synthesis and biol. evaluation of an HPD subtype (4, IV) featuring a cyclohexylmethyl group at the C-6 position. Antiviral testing showed that most analogs of 4 inhibited HIV-1 in the low nanomolar to submicromolar range, without cytotoxicity at concentrations up to 100 μM. Biochem., these analogs dually inhibited both the polymerase (pol) and the RNase H functions of RT, but not INST. Co-crystal structure of 4a (IV; R¹ = i-Pr, R² = H) with RT revealed a nonnucleoside RT inhibitor (NNRTI) binding mode. Interestingly, chemotype 11, the synthetic precursor of 4 lacking the 3-OH group, did not inhibit RNase H while potently inhibiting pol. By virtue of the potent antiviral activity and biochem. RNase H inhibition, HPD subtype 4 could provide a viable platform for eventually achieving potent and selective RNase H inhibition through further medicinal chem. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Recommanded Product: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Organophosphorus compounds with β-cyanoethyl-type structural components. I. Synthesis of β-cyanoethylated amidophosphites and phosphoramides was written by Petrov, Pavel;Vlad, Florin-Iosif;Muresan, Sorel;Valceanu, Radu. And the article was included in Revista de Chimie (Bucharest) in 1996.Product Details of 7528-78-1 This article mentions the following:

This article presents studies performed on obtaining some β-cyanoethylated phosphonamides and phosphoramides, as well as their possible use. Thus, reaction of di-Me phosphite, PCl₃, or POCl₃ with a mixture of NH(CH₂CH₂CN)₂ and N(CH₂CH₂CN)₃ gave (MeO)₂P(O)N(CH₂CH₂CN)₂, P[N(CH₂CH₂CN)₂]₃, or P(O)[N(CH₂CH₂CN)₂]₃, resp. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Product Details of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Product Details of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Binding interactions and FRET between bovine serum albumin and various phenothiazine-/anthracene-based dyes: a structure-property relationship was written by Bhuin, Shouvik;Halder, Sayantan;Saha, Subit Kumar;Chakravarty, Manab. And the article was included in RSC Advances in 2021.Application of 55490-87-4 This article mentions the following:

The present study demonstrates binding interactions and Forster resonance energy transfer (FRET) between bovine serum albumin (BSA) and a series of structurally and electronically diverse phenothiazine (PTZ) and anthracene (ANT) dyes. Upon selective excitation of tryptophan (Trp) residues of BSA, radiationless energy transfer to a dye takes place, resulting in fluorescence quenching of the former. Fluorescence quenching mechanisms, FRET parameters, possible locations, and binding constants of dyes with the BSA have been examined to deduce a structure-property relationship. The mechanism of quenching is apparently static in nature. PTZ dyes with heteroatoms and a pentyl tail (C5-PTZ) attached to them were found to have a stronger binding affinity with BSA as compared to ANT dyes. Stronger binding affinities of C5-PTZ dyes with BSA result in greater energy transfer efficiencies (ET). A dye with a strong electron-withdrawing group present in it has shown better energy accepting capability. A FRET study with dicyanoaniline (DCA) analogs of PTZ and ANT dyes (C5-PTZDCA and ANTDCA, resp.) revealed that ET depends on electronic and structural factors of mols. An almost orthogonal geometry between ANT and DCA moieties (�9°) in ANTDCA induces the greater extent of electron transfer from ANT to DCA, showing a higher ET for this dye as compared to C5-PTZDCA in which the torsion angle is only �8°. Further, the observed facts have been validated by exptl. determined bandgaps (using cyclic voltammetry experiments) for all the dyes. Thus, the hydrophobic character and the presence of interactive substituents along with the electron-accepting abilities majorly control the FRET for such dyes with BSA. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Meisenheimer-type adducts from thiophene derivatives. Part 7. Interdependence of ¹³C NMR, thermodynamic and kinetic data was written by Dell’Erba, Carlo;Sancassan, Fernando;Novi, Marino;Spinelli, Domenico;Consiglio, Giovanni. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1991.HPLC of Formula: 42137-24-6 This article mentions the following:

A ¹³C NMR study has been carried out in (CD₃)₂SO on the thiophene derivatives I (X = H, Ac, CN, etc.; R = H) and II (same X, R) and the related Meisenheimer adducts III and IV. The data obtained, and in particular the sums of the chem.-shift changes (∑ΔÎ? at C-3, C-4 and C-5, accompanying the formation of the adducts, are compared with the corresponding data previously obtained for analogous substrates I (same X, R = MeO) and II (same X, R = MeO) and adducts III and IV. The four series of ∑ΔÎ?values are then examined in the light of the already reported thermodn. (K_e) and kinetic (k₁) constants for the formation of the adducts. For a given X-substituent, log K_e values increase linearly as the corresponding absolute ∑ΔÎ?values decrease. On these grounds, the smaller π-electron-d. rearrangement accompanying the formation of gem-dimethoxy adducts emerges as an important factor, contributing to the larger observed K_e values. A further outcome is that, within a single series of adducts, a linear relationship of either log K_e or log₁ with ∑ΔÎ?holds only when excluding the terms with X = Ac or NO₂. Such findings are interpreted on the basis of the two-component nature of the substituent R effects: while for the nitro and the acetyl substituents the π-electron acceptor component is prevalent, the stabilizing effect of the other substituents is due mainly to a charge-dipole interaction. The anal. of some literature data for the benzene series fits the above conclusions. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6HPLC of Formula: 42137-24-6).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.HPLC of Formula: 42137-24-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Phototranspositions of cyanothiophenes: permutation pattern analysis and the chemical trapping of an intermediate 5-thiabicyclo[2.1.0]pent-2-ene was written by Barltrop, John A.;Day, A. Colin;Irving, Edward. And the article was included in Journal of the Chemical Society, Chemical Communications in 1979.SDS of cas: 55406-13-8 This article mentions the following:

Through their first excited singlet states, cyanothiophenes undergo phototranspositions for which permutation pattern anal. and the isolation of furan-thiabicyclopentene adducts (from irradiation in furan), suggest a mechanism involving 2,5-bonding followed by a ‘walk’ of the S atom. E.g., irradiation of 3-cyanothiophene in furan gave 71 and 7% resp., of the 1:1 adducts I and II. This result provides evidence for the intermediate III, for which I and II are the expected Diels-Alder adducts with furan; a similar result occurred with 2-cyanothiophene. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8SDS of cas: 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. SDS of cas: 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design and synthesis of novel tranilast analogs: Docking, antiproliferative evaluation and in-silico screening of TGFβR1 inhibitors was written by Ismail, Magda M. F.;El-Zahabi, Heba S. A.;Ibrahim, Rabab S.;Mehany, Ahmed B. M.. And the article was included in Bioorganic Chemistry in 2020.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

This work summarizes design, synthesis and biol. evaluation of sixteen novel tranilast analogs I [X = F, Cl, Br], II [X = F, O₂N], [X = H, Me; R¹ = OMe, Cl; R² = H, Cl], IV [Ar = 2-thiophenyl, 2,4-dimethylphenyl, 4-pyridinyl] and V [R = cyano, ethoxycarbonyl] on different tumors such as PC-3, HepG-2 and MCF-7 cell lines. The in-vitro cytotoxicity was evaluated using MTT assay showed that, twelve compounds out of sixteen showed higher cytotoxic activities (IC₅₀‘s 1.1-6.29μM), than that of the reference standard, 5-FU (IC₅₀ 7.53μM). The promising cytotoxic hits II [X = F], IV [Ar = 2-thiophenyl] and V [R = CN, X = 2,5-dimethoxy, n = 1; R = CN, X = OH, 2,5-dimethoxy, n = 0] proved to be selective to cancer cells when their cytotoxicity’s are examined on human normal cell line (WI-38). Then they were investigated for their possible mode of action as TGFβR1 inhibitors; remarkable inhibition of TGFβR1 by these hits was observed at the range of IC₅₀ 0.087-3.276μM. The cell cycle anal. of the most potent TGFβR1 inhibitor, II [X = O₂N] revealed cell cycle arrest at G2/M phase on prostate cancer cells. Addnl., it was clearly indicated apoptosis induction at Pre-G1 phase, this was substantiated by significant increase in the expression on the tumor suppressor gene, p53 and up regulation the level of apoptosis mediator, caspase-3. In addition, in-silico study was performed for validating the physicochem. and ADME properties which revealed that, all compounds were orally bioavailable with no side effects complying with Lipinski rule. The proposed mode of action was further explored on the light of mol. modeling simulation of the most potent compounds, II [X = O₂N] and V [n = 0, R = CN, X = 2,5-dimethoxy] which were docked into the active sites of TGFβR1 to predict their affinities toward the receptor. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rearrangement of the bromine atom in the demethylation of bromomethoxybenzoic acid. IV. 2-Bromoanisic acid and 3-bromoanisic acid was written by Tomita, Masao;Fujitani, Kazuyoshi. And the article was included in Yakugaku Zasshi in 1956.Related Products of 82380-17-4 This article mentions the following:

2,4-Br(MeO)C₆H₃CO₂H (XI), needles, m. 197-8°, was synthesized from 4-O₂NC₆H₄Me or p-cresol as a raw material. Nitration of 3-BrC₆H₄OH gave 3,4-Br(O₂N)C₆H₃OH, m. 125-31°, which was reduced to 3,4-Br(H₂N)C₆H₃OH, m. 151°; this was diazotized and treated with CuCN yielding 2,4-Br(HO)C₆H₃CN (XII), m. 151°. XI (0.5 g.), 15 ml. PhCl, and 2 g. AlCl₃ heated 1.5 hrs. on a water bath and the product poured on ice and extracted with Et₂O gave 0.3 g. 2,4-Br(HO)C₆H₃CO₂H (XIII), needles, m. 206-8° (from water); the m.p. of XIII given as 151° by Hodgson and Jenkinson (cf. C.A. 22,949) was confirmed to be the m.p. of XII. XI (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated 5 hrs. at 130° and 2 hrs. at 150°, the product concentrated, neutralized with NaHCO₃ to remove the acidic substance, extracted with Et₂O, stirred with NaOH, and the NaOH layer acidified with HCl and extracted with Et₂O gave 3-BrC₆H₄OH (benzoate, m. 84-5°) and a small amount of XIII, m. 206-8°. XI (0.5 g.) and 6 ml. HCl-AcOH in a sealed tube heated 12 hrs. at 150° gave 0.45 g. XI. 2,4-Br(MeO)C₆H₃CO₂Me (XIV), plates, m. 29°, (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated and the product treated as usual gave 3-BrC₆H₄OH. Similarly, 3,4-Br(MeO)C₆H₃CO₂H gave 3,4-Br(HO)C₆H₃CO₂H, m. 106-7°. 3,4-Br(MeO)C₆H₃CO₂Me (0.5 g.) gave 0.3 g. 3,5,4-Br₂(HO)C₆H₂CO₂H, m. 253-7° (decomposition), and 0.1 g. 3,4-Br(HO)C₆H₃CO₂H, m. 175-7° (Me ester, m. 107°). In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Related Products of 82380-17-4).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Related Products of 82380-17-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide was written by Kiyani, Hamzeh;Daroonkala, Masoumeh Darzi. And the article was included in Bulletin of the Chemical Society of Ethiopia in 2015.Related Products of 51473-74-6 This article mentions the following:

An efficient procedure for the synthesis of various 3-substituted coumarins I [R = H, 6-Br, 7-NEt₂, 8-OMe; R¹ = CN, COOH; X = O] as well as 2-imino-2H-chromenes I [R¹ = CN; X = NH] was developed via potassium phthalimide-catalyzed Knoevenagel condensation reaction of salicylaldehydes with active methylene compounds under aqueous conditions at room temperature This approach provided many merits such as high yields of products, simple work-up procedure, waste free and mild reaction conditions, com. available organocatalyst and the use of water as environmentally benign solvent. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Related Products of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts