Month: January 2023

Antituberculous compounds. III. p-Alkoxy-N-arylbenzamidines was written by Partridge, M. W.. And the article was included in Journal of the Chemical Society in 1949.Electric Literature of C11H13NO This article mentions the following:

As an extension of experiments on the relation between structure and activity against Mycobacterium tuberculosis of N-substituted amidines, a series of p-alkoxy-N-arylbenzamidines and certain analogs have been prepared Although high activities were observed in vitro in several cases, no activity could be demonstrated in vivo. p-NCC₆H₄ONa (prepared with 1 equivalent of Na in EtOH) and 1 equivalent of RCl, refluxed 16-20 h., give the following p-alkoxylphenyl cyanides (I), p-ROC₆H₄CN (R given): Pr, b₃ 121-2°, m. 47°, 54%; Bu, b₃ 146-8°, m. 35°, 80%; hexyl, b₃ 155-7°, m. 32°, 71%; octyl, b₂ 171-3 °, 70%; allyl, m. 43°, 72%; iso-Bu, b₁ 114-16°, 35%. The I and an equivalent of an arylammonium benzenesulfonate, heated 1-4 h. at 180-210°, give the following N-phenylbenzamidines, p-ROC₆H₄C(:NH)NHPh (R given): Me (benzenesulfonate, m. 186-7°, 51%); Et, m. 143.5-4.5°, 55% (benzenesulfonate, m. 168-9°); Pr, m. 128-9°, 72%; Bu, m. 121-2°, 90%; iso-Bu, m. 131-2°, 88%; allyl, m. 115-17°, 28% (low yield a result of reduced heating period to avoid Claisen rearrangement of the cyanide); hexyl, m. 122-4°, 90%; octyl, m. 118-19°, 90%. p-MeOC₆H₄CN (13.3 g.) and 9.4 g. 2-aminopyridine at 60°, treated (5 min.) with 13.3 g. AlCl₃ and heated 20 min. at 200°, give 5.4 g. unchanged p-MeOC₆H₄CN and 24% p-methoxy-N-(2-pyridyl)benzamidine, m. 107-8°. p-MeOC₆H₄C(:NPh)Cl (30 g.) and 12 g. PhNH₂ in 100 cc. C₆H₆, refluxed 3 h., give 78% of the chloride, m. 269-70° (decomposition), of p-methoxy-N,N’-diphenylbenzamidine, m. 107-8°. p-BuOC₆H₄COCl (51.2 g.) and 70 cc. 2 N NaOH, gradually added to 22.3 g. PhNH₂ in 50 cc. 2 N NaOH, give 76% p-butoxybenzanilide (II), m. 147°; II, PhNH₂, and PCl₅ give 96% p-butoxy-N,N’-diphenylbenzamidine, m. 111°. p-H₂NC₆H₄CO₂Et and PhSO₃H give p-carbethoxyanilinium benzenesulfonate, m. 194-5°; p-butoxy-N-(p-carbethoxyphenyl)benzamidine, m. 138.5-9.5°, 43%; refluxed 6 h. with 5 N NaOH, there results 78% of the free acid, m. 249-50° (decomposition). p-Butoxy-N-(p-chlorophenyl)benzamidine, m. 151-2°, 50%; N-(p-butoxyphenyl) analog, m. 149-50°, 60%. The relation between structure and activity of these compounds against M. tuberculosis is discussed. The activities of the more active members of this series are decreased by serum, although some of the compounds retain activities of the order of 1:100,000. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6Electric Literature of C11H13NO).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Electric Literature of C11H13NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of strontium ranelate was written by Xu, Yan;Su, Man;Qu, Chun-sheng. And the article was included in Qilu Yaoshi in 2012.Product Details of 58168-20-0 This article mentions the following:

The synthesis of strontium ranelate was studied. The strontium ranelate was synthesized from citric acid by decarboxylation, esterification, cyclization, alkylation, hydrolyzation and then salt formation. The structure of strontium ranelate was confirmed by IR, ¹H-NMR, ¹³C-NMR and the total yield was approx. 41.4%. This synthesis route was simple with low cost and high purity, and it was suitable for industrial production In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Product Details of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy was written by Jiang, Hui-Min;Qin, Jing-Hao;Sun, Qing;Zhang, Dong;Jiang, Jin-Peng;Ouyang, Xuan-Hui;Song, Ren-Jie;Li, Jin-Heng. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 10282-32-3 This article mentions the following:

A copper-promoted reductive cross-coupling of nitroarenes RNO₂ (R = Ph, 4-iodiphenyl, pyridin-3-yl, etc.) with 4-alkyl-1,4-dihydropyridines I (R¹ = Pr, cyclohexyl, Bn, etc.) for producing N-alkylbenzenamines RNHR¹ is described. Using 4-alkyl-1,4-dihydropyridines I as alkyl radical sources and internal reducing agents enables the construction of C(sp³)-N bonds under oxidative conditions, which provide an elegant complementary platform to assemble N-alkylbenzenamines with good tolerance for sensitive functional groups. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Property Focused Structure-Based Optimization of Small Molecule Inhibitors of the Protein-Protein Interaction between Menin and Mixed Lineage Leukemia (MLL) was written by Borkin, Dmitry;Pollock, Jonathan;Kempinska, Katarzyna;Purohit, Trupta;Li, Xiaoqin;Wen, Bo;Zhao, Ting;Miao, Hongzhi;Shukla, Shirish;He, Miao;Sun, Duxin;Cierpicki, Tomasz;Grembecka, Jolanta. And the article was included in Journal of Medicinal Chemistry in 2016.Quality Control of 5-Methyl-2-nitrobenzonitrile This article mentions the following:

Development of potent small mol. inhibitors of protein-protein interactions with optimized druglike properties represents a challenging task in lead optimization process. Here, we report synthesis and structure-based optimization of new thienopyrimidine class of compounds, which block the protein-protein interaction between menin and MLL fusion proteins that plays an important role in acute leukemias with MLL translocations. We performed simultaneous optimization of both activity and druglike properties through systematic exploration of substituents introduced to the indole ring of lead compound 1 (MI-136) to identify compounds suitable for in vivo studies in mice. This work resulted in the identification of compound 27 (MI-538), which showed significantly increased activity, selectivity, polarity, and pharmacokinetic profile over 1 and demonstrated a pronounced effect in a mouse model of MLL leukemia. This study, which reports detailed structure-activity and structure-property relationships for the menin-MLL inhibitors, demonstrates challenges in optimizing inhibitors of protein-protein interactions for potential therapeutic applications. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Quality Control of 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. 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. Quality Control of 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Antihypertensive activity of 6-arylpyrido[2,3-d]pyrimidin-7-amine derivatives was written by Bennett, Lawrence R.;Blankley, C. John;Fleming, Robert W.;Smith, Ronald D.;Tessman, Deirdre K.. And the article was included in Journal of Medicinal Chemistry in 1981.Category: nitriles-buliding-blocks This article mentions the following:

Fifty-one title compounds I (R = H, Me, Et, etc.; R¹ = H, Me, OEt, etc.; R² = substituted phenyl) were synthesized and evaluated for antihypertensive activity in the conscious spontaneously hypertensive rat. A number of these compounds, notably 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine [76574-80-6], lowered blood pressure in these rats in a gradual and sustained manner to normotensive levels at oral doses of 10-50 mg/kg. Normalized blood pressure levels could then be maintained by single daily oral doses. The effect of structural variation in the 6-aryl group and in the 2 and 4 positions of the pyridopyrimidine ring on activity is reported and discussed. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9Category: nitriles-buliding-blocks).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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. Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photolysis of 1-aryl-3,3-dialkyltriazenes was written by Lippert, Th.;Stebani, J.;Nuyken, O.;Stasko, A.;Wokaun, A.. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 1994.Reference of 4714-63-0 This article mentions the following:

The photolytic decomposition of substituted 1-phenyl-3,3-diethyl-triazenes has been studied using both pulsed XeCl^* excimer excitation at 308 nm, and continuous-wave irradiation with a xenon lamp. Electron-withdrawing substituents in the para position at the Ph ring are found to decrease both the quantum yield of photolysis and the apparent first-order rate constant of decomposition The reaction proceeds according to an overall one-step pathway; anal. of the photolysis products by gas chromatog.-mass spectrometry is consistent with a radical decomposition mechanism. For the compound 1-(4-nitrophenyl)-3,3-diethyl-triazene, an autocatalytic acceleration of the photolysis was observed during the continuous-wave irradiation, using a xenon lamp source. This phenomenon is analyzed in terms of an involvement of the nitro group: photoreduction of the latter functionality involves the creation of solvent radicals in comparatively large concentrations, which are detected by in-situ ESR experiments These radicals may attack and decompose further mols. of the starting material. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Reference of 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Reference of 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2-Amino-thiophene derivatives present antileishmanial activity mediated by apoptosis and immunomodulation in vitro was written by Rodrigues, Klinger Antonio da Franca;Dias, Cinthia Nobrega de Sousa;Neris, Patricia Lima do Nascimento;Rocha, Juliana da Camara;Scotti, Marcus Tullius;Scotti, Luciana;Mascarenhas, Sandra Rodrigues;Veras, Robson Cavalcante;Almeida de Medeiros, Isac;Keesen, Tatjana de Souza Lima;Bento de Oliveira, Tiago;Alves de Lima, Maria do Carmo;Balliano, Tatiane Luciano;Mendonca de Aquino, Thiago;Olimpio de Moura, Ricardo;Junior, Francisco Jaime Bezerra Mendonca;de Oliveira, Marcia Rosa. And the article was included in European Journal of Medicinal Chemistry in 2015.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

This study evaluated the effects of 2-amino-thiophene derivatives on the promastigote and amastigote forms of Leishmania amazonensis and their possible mechanisms of action. Initially, the authors evaluated the antileishmanial activity of ten 2-amino-thiophene derivatives on promastigote and axenic amastigote forms of Leishmania amazonensis and their cytotoxicity against murine macrophages and human red blood cells. Three promising compounds were selected for studies of the cell death process using flow cytometry anal. and a DNA fragmentation assay. The effects of the compounds were assessed on intramacrophagic amastigotes, and the modulation of cytokine and NO production was investigated. All thiophene derivatives showed antileishmanial activity against promastigotes and axenic amastigotes with less toxicity for murine macrophages and human red blood cells. The best values were obtained for compounds containing a lateral indole ring. Docking studies suggested that these compounds played an important role in inhibiting trypanothione reductase (TryR) activity. The selected compounds SB-200, SB-44, and SB-83 induced apoptosis in promastigotes involving phosphatidylserine externalization and DNA fragmentation in a pattern similar to that observed for the pos. control. Addnl., SB-200, SB-44, and SB-83 significantly reduced the infection index of macrophages by the parasites; for compounds SB-200 and SB-83 this reduction was associated with increased TNF-α, IL-12, and NO levels. This study demonstrated the effective and selective action of 2-amino-thiophene derivatives against L. amazonensis, resulting in apoptosis-like cell death and immunomodulation in vitro. The results suggest that they are promising compounds for the development of new leishmanicidal drugs. 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. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Spectroscopic and theoretical studies of arylmethylenemalonodinitriles. I. Electronic spectra was written by Kaneti, J.;Vitanov, D.;Yuchnovski, I.;Yuritsin, V.. And the article was included in Izvestiya po Khimiya in 1978.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

The UV invisible absorption spectra of arylmethylene (aryl = substituted Ph, 1-naphthyl, 4-biphenylyl, 9-anthryl, etc.) of malonodinitrile are studied using PPP MO calculations The electronic spectra are similar to those of polyenes with the same mol. topol. The introduction of cyano groups in the conjugated system does not give rise to charge-transfer states. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A novel adenine-based zinc(II) metal-organic framework featuring the Lewis basic sites for heterogeneous catalysis was written by Zhang, Shixing;He, Hongming;Sun, Fuxing;Zhao, Nian;Du, Jianshi;Pan, Qinhe;Zhu, Guangshan. And the article was included in Inorganic Chemistry Communications in 2017.HPLC of Formula: 55490-87-4 This article mentions the following:

Metal-organic frameworks (MOFs), as a new sort of crystalline materials, have attracted lots of interest in many applications during the past decades. Recently, many efforts were focused on the development of MOFs as heterogeneous catalysis. The authors selected adenine (ad) and tetracarboxylic acid, 5,5′-(1,3,6,8-tetraoxobenzo[Imn] Li et al. (1999), He et al. (2016) phenanthroline-2,7-diyl)bis-1,3-benzenedicarboxylic acid (H₄L), as organic linkers to assemble with Zn(II) ions to construct a novel adenine-based porous MOF. There are three different inorganic clusters in the framework, including ZnO₂N₂, Zn₂O₂N₆, and ZnO₅N clusters. Interesting, the resultant porous MOF, [H₂NMe₂]·[Zn₄(L)_1.5(ad)₃(H₂O)₂]·4DMF, retains free amino groups in the framework, which can be served as Lewis basic sites to catalyze Knoevenagel condensation reaction. The catalytic study exhibits that the as-synthesized MOF with free amino groups can be used as heterogeneous catalysis with remarkable catalytic efforts and good recycle. CCDC 1501692. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4HPLC of Formula: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

One-pot Reductive Amination of carbonyl Compounds with Nitro Compounds by Transfer Hydrogenation over Co-N_x as catalyst was written by Zhou, Peng;Zhang, Zehui. And the article was included in ChemSusChem in 2017.Formula: C14H12N2 This article mentions the following:

A new method was developed for the synthesis of secondary amines through the one-pot reductive amination of carbonyl compounds with nitro compounds using formic acid as the hydrogen donor over a heterogeneous non-noble-metal catalyst (Co-N_x/C-800-AT, generated by the pyrolysis of the cobalt phthalocyanine/silica composite at 800° under a N₂ atmosphere and subsequent etching by HF). Both nitrogen and cobalt were of considerable importance in the transfer hydrogenation reactions with formic acid. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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.Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts