Tag: 100-200

Dichlorophenylacrylonitriles as AhR Ligands That Display Selective Breast Cancer Cytotoxicity in vitro was written by Baker, Jennifer R.;Gilbert, Jayne;Paula, Stefan;Zhu, Xiao;Sakoff, Jennette A.;McCluskey, Adam. And the article was included in ChemMedChem in 2018.Category: imidazoles-derivatives This article mentions the following:

Knoevenagel condensation of 3,4-dichloro- and 2,6-dichlorophenylacetonitriles gave a library of dichlorophenylacrylonitriles. Our leads (Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile (5) and (Z)-2-(3,4-dichlorophenyl)-3-(4-nitrophenyl)acrylonitrile (6) displayed 0.56±0.03 and 0.127±0.04 μM growth inhibition (GI₅₀) and 260-fold selectivity for the MCF-7 breast cancer cell line. A 2,6-dichlorophenyl moiety saw a 10-fold decrease in potency; addnl. nitrogen moieties (-NO₂) enhanced activity (Z)-2-(2,6-dichloro-3-nitrophenyl)-3-(2-nitrophenyl)acrylonitrile (26) and (Z)-2-(2,6-dichloro-3-nitrophenyl)-3-(3-nitrophenyl)acrylonitrile (27), with the corresponding -NH₂ analogs (Z)-2-(3-amino-2,6-dichlorophenyl)-3-(2-aminophenyl)acrylonitrile (29) and (Z)-2-(3-amino-2,6-dichlorophenyl)-3-(3-aminophenyl)acrylonitrile (30) being more potent. Despite this, both 29 (2.8±0.03 μM) and 30 (2.8±0.03 μM) were found to be 10-fold less cytotoxic than 6. A bromine moiety effected a 3-fold enhancement in solubility with (Z)-3-(5-bromo-1H-pyrrol-2-yl)-2-(3,4-dichlorophenyl)acrylonitrile 18 relative to 5 at 211 μg mL^-1. Modeling-guided synthesis saw the introduction of 4-aminophenyl substituents (Z)-3-(4-aminophenyl)-2-(3,4-dichlorophenyl)acrylonitrile (35) and (Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide (38), with resp. GI₅₀ values of 0.030±0.014 and 0.034±0.01 μM. Other analogs such as 35 and 36 were found to have sub-micromolar potency against our panel of cancer cell lines (HT29, colon; U87 and SJ-G2, glioblastoma; A2780, ovarian; H460, lung; A431, skin; Du145, prostate; BE2-C, neuroblastoma; MIA, pancreas; and SMA, murine glioblastoma), except compound 38 against the U87 cell line. A more extensive evaluation of 38 ((Z)-N-(4-(2-cyano-2-(3,4-dichlorophenyl)vinyl)phenyl)acetamide) in a panel of drug-resistant breast carcinoma cell lines showed 10-206 nM potency against MDAMB468, T47D, ZR-75-1, SKBR3, and BT474. Mol. Operating Environment docking scores showed a good correlation between predicted binding efficiencies and observed MCF-7 cytotoxicity. This supports the use of this model in the development of breast-cancer-specific drugs. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Category: imidazoles-derivatives).

1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Connection between dielectric constant and total number of hydrogen-bond groups per cation-anion pair in ionic liquids was written by Shi, Baoli. And the article was included in Journal of Molecular Liquids in 2020.Application of 35487-17-3 This article mentions the following:

This paper reports a quant. connection between the dielec. constant and calculated total number of hydrogen-bond groups per cation-anion pair for 44 ionic liquids, including 15 ionic liquids with high dielec. constants exceeding 20. The total number of hydrogen-bond groups per cation-anion pair was equal to the addition of the hydrogen-bond group number per cation and per anion. The methylene group could reduce the group number capable of forming hydrogen bonds, and one methylene group caused a decrease of 1 hydrogen-bond number Regardless of whether a liquid was ionic or non-ionic liquid, approx. linear relationship were observed between dielec. constant and total hydrogen-bond number per mol. For ionic liquids, an increase of 1 in the total number of hydrogen-bond groups per cation-anion pair resulted in an increase of approx. 8.5 in the dielec. constant For non-ionic liquids, the value was approx. 21.9. The average molar d. of nine hydrogen-bonded ionic liquids with high dielec. constants was 9.3 x 10³ mol/m³, while the average molar d. of eight non-ionic liquids with hydrogen-bonds was 21.1 x 10³ mol/m³. The 21.1 M d. coefficient of the non-ionic liquids was almost equal to the 21.9 coefficient in the dielec. constant equation, and the 9.3 M d. coefficient of the ionic liquids was very close to the 8.5 coefficient in its dielec. constant equation. This result indicated that the effect mechanisms of the intermol. hydrogen-bond structure on dielec. constant were similar for the two types of liquids In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Application of 35487-17-3).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Application of 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Nitroimidazole-based ‘extruded mustards’ designed as reductively activated hypoxia-selective cytotoxins was written by Hay, Michael P.;Denny, William A.;Wilson, William R.. And the article was included in Anti-Cancer Drug Design in 1996.Synthetic Route of C5H5N3O4 This article mentions the following:

A new class of nitroimidazole alkanoic acid amides, designed to extrude para-aminophenyl mustard by intramol. cyclization following reduction of the nitro group, have been prepared and evaluated for their ability to function as bioreductively activated prodrugs. The mechanism of activation following (bio)reduction was studied using the model compounds and the related mustard analogs. However, the reduced forms of these compounds were relatively stable and not susceptible to intramol. cyclization. This is in contrast to the corresponding 2-nitrophenylalkyl amides, where the hydroxylamino or amino reduction products undergo intramol. cyclization via a tetrahedral intermediate, resulting in cleavage of the amide and release of an activated aromatic mustard. One of the 2-nitroimidazole mustards (I) had 20-fold greater toxicity towards aerobic AA8 cells than RB 6145, and a 51-fold greater toxicity towards UV4 cells (which are defective in DNA cross-link repair and thus hypersensitive to crosslinking agents). The cytotoxicity of I against AA8 cells was enhanced 3.3-fold under hypoxic conditions, but the compound was inactive against the hypoxic subfraction of cells in KHT tumors in vivo. In the experiment, the researchers used many compounds, for example, 2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7Synthetic Route of C5H5N3O4).

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (cas: 22813-32-7) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Synthetic Route of C5H5N3O4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

New class of non-symmetrical homo-dibenzimidazolium salts and their dinuclear Silver(I) di-NHC complexes was written by Haziz, Umie F. M.;Haque, Rosenani A.;Amirul, A. A.;Aidda, O. Noor;Razali, Mohd. R.. And the article was included in Journal of Organometallic Chemistry in 2019.Electric Literature of C8H8N2 This article mentions the following:

This work describes the synthesis of an uncommon non-sym. dibenzimidazolium salts as a precursor for the dinuclear Ag(I) di-NHC complexes with a formula of [Ag₂L₂]·2PF₆ (L = NHC = bis-N-heterocyclic carbene). Through the reaction of 3-(2-bromoethyl)-1-butylbenzimidazole bromide with n-alkylbenzimidazole (alkyl = Me, Et, Pr, pentyl, hexyl, heptyl, benzyl), seven non-sym. dibenzimidazolium bromide salts, 1–3 and 5–8 were obtained. The sym. dibenzimidazolium bromide salt 4 was obtained either as a minor product or through the reaction between n-butylbenzimidazole with 1,2-dibromoethane in 2:1 M ratio. Salts 1–8 were then reacted with Ag₂O via in-situ deprotonation method to facilitate the formation of dinuclear Ag(I) di-NHC complexes, 9–16. The formation of these complexes is confirmed by the disappearance of both H2′ peaks in ¹H NMR and the presence of carbene peaks in the range of 187-191 ppm in the ¹³C NMR of the complexes. From single crystal X-ray diffraction study, complex 16 is determined to be a dinuclear complex bearing dicarbene ligands which is further stabilized by significant argentophilic interaction with the separation of Ag···Ag being 3.358(5) Å. All the bis-benzimidazolium salts 1–8 show no activities while all dinuclear Ag(I) di-NHC complexes, 9–16 show medium to higher activities against E. coli (ATCC 25922) and S. aureus (ATCC 12600) compared to the standard antibiotic drug, Ampicillin. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Electric Literature of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Electric Literature of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents was written by Hsieh, Sheng-Ying;Bode, Jeffrey W.. And the article was included in ACS Central Science in 2017.Category: imidazoles-derivatives This article mentions the following:

The authors report that the inclusion of Lewis acids in photocatalytic reactions of organosilanes allows access to a distinct reaction pathway featuring an Ir(III)^*/Ir(IV) couple instead of the previously employed Ir(III)^*/Ir(II) pathway, enabling the transformation of aromatic and aliphatic aldehydes to thiomorpholines and thiazepanes. The role of the Lewis acid in accepting an electron-either directly or via coordination to an imine-can be extended to other classes of photocatalysts and transformations, including oxidative cyclizations. The combination of light induced reactions and Lewis acids therefore promises access to new pathways and transformations that are not viable using the photocatalysts alone. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Category: imidazoles-derivatives).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Preparation and physicochemical study of copper(II) and nickel(II) chelates with aroylhydrazones of 1-methyl-2-acylbenzimidazole was written by Lukov, V. V.;Abramova, N. A.;Kogan, V. A.;Anisimova, V. A.;Starikova, A. G.;Bondarenko, G. I.. And the article was included in Zhurnal Neorganicheskoi Khimii in 1988.SDS of cas: 3012-80-4 This article mentions the following:

I (R = H, Me; R¹ = H, p-MeO, m-NO₂, p-Me₂N) was prepared from the corresponding 1-methyl-2-acylbenzimidazole and H₂NNHC(O)C₆H₄R¹. M(OAc)₂ (M = Cu, Ni) reacted with I (HL) to give ML₂. CuX₂ reacted with I to give CuLX (X = Cl, R = H, R¹ = H, m-NO₂, p-NMe₂; X = Cl, Br, R = Me, R¹ = p-OMe). The complexes were characterized by IR spectra and magnetic moment measurements. NiL₂ were characterized by electronic spectra and several CuL₂ by ESR. In CuL₂, L^– are bidentate coordinating through the hydrazone N and O atoms. In NiL₂ and in CuLX, L^– are tridentate, coordinating via the imidazole N, hydrazone N and O atoms. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4SDS of cas: 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.SDS of cas: 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling was written by Firmansyah, Dikhi;Banasiewicz, Marzena;Gryko, Daniel T.. And the article was included in Organic & Biomolecular Chemistry in 2015.Synthetic Route of C7H5BrN2 This article mentions the following:

The anion-radical coupling of structurally diverse series of aromatic compounds possessing biaryl linkages led to seven fused, polycyclic heterocycles e. g., I, in reasonable yields. The yield of the key step (K, toluene, O₂) depends on both electronic and steric factors. The whole strategy consists of just two steps starting from an unsubstituted imidazo[1,2-a]pyridine, giving target compounds in an overall yield of 4-34%. The same strategy also works for derivatives of imidazo[1,5-a]pyridine. A new process has been discovered for such vertically-expanded imidazo[1,2-a]pyridines, consisting of a sequential Diels-Alder reaction followed by a retro-Diels-Alder reaction. The optical properties of the library of π-expanded imidazo[1,2-a]pyridines were for the first time fully characterized, showing that fluorescence quantum yields are significantly lower than for the singly-linked compounds In the experiment, the researchers used many compounds, for example, 5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1Synthetic Route of C7H5BrN2).

5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Synthetic Route of C7H5BrN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Catalytic asymmetric cycloaddition of CO₂ to epoxides via chiral bifunctional ionic liquids was written by Duan, Shuhui;Jing, Xinyao;Li, Dandan;Jing, Huanwang. And the article was included in Journal of Molecular Catalysis A: Chemical in 2016.Synthetic Route of C11H20N2 This article mentions the following:

A series of new chiral ionic liquid catalysts composed of the N,N’-bis(salicyclidene) cyclohexene diaminatocobalt and an imidazolium salt were designed, prepared and applied for the chiral cyclic carbonate synthesis from racemic epoxides and carbon dioxide. All reactions exhibit good enantioselectivity for the chiral cyclic carbonate without polycarbonate and other byproducts. The order of The order of catalytic activity toward the axial anions is OAc^– > CF₃CO^–₂ > CCl₃CO^–₂ > OTs^– and the order of enantioselectivity is OTs^– > OAc^– > CCl₃CO^–₂ > CF₃CO^–₂. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Synthetic Route of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Synthetic Route of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Studies of imidazo[1,2-a]benzimidazoles 32. Synthesis and properties of 2,3-dihydroimidazo- and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazol-9(10)-ylacetic acids was written by Anisimova, V. A.;Tolpygin, I. E.;Askalepova, O. I.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2014.Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole This article mentions the following:

Reaction of unsubstituted 2,9-dihydro-3H-imidazo- and 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazoles with haloacetates afforded the corresponding hetaryl-9(10)-acetates. Subsequent base and acid hydrolysis of these esters yielded the corresponding acids. The zwitterionic structure of the latter was proved. They were also prepared by direct alkylation of unsubstituted N-heterocycles using ClCH₂CO₂Na or by hydrolysis of the resp. acetonitriles. The synthesized esters readily underwent aminolysis and hydrazinolysis. In the experiment, the researchers used many compounds, for example, 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole).

2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole (cas: 24134-26-7) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Application In Synthesis of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Silica-immobilized ionic liquid Bronsted acids as highly effective heterogeneous catalysts for the isomerization of n-heptane and n-octane was written by Dhar, Abhishek;Siva Kumar, Nadavala;Khimani, Mehul;Al-Fatesh, Ahmed S.;Ibrahim, Ahmed A.;Fakeeha, Anis H.;Patel, Hiren;Vekariya, Rohit L.. And the article was included in RSC Advances in 2020.Quality Control of 1-Methylbenzimidazole This article mentions the following:

Metal-free imidazolium-based ionic liquid (IL) Bronsted acids 1-Me imidazolium hydrogen sulfate [HMIM]HSO₄ and 1-Me benzimidazolium hydrogen sulfate [HMBIM]HSO₄ were synthesized. Their physicochem. properties were investigated using spectroscopic and thermal techniques, including UV-Vis, FT-IR, ¹H NMR, ¹³C-NMR, mass spectrometry, and TGA. The ILs were immobilized on mesoporous silica gel and characterized by FT-IR spectroscopy, SEM, Brunauer-Emmett-Teller anal., ammonia temperature-programmed desorption, and thermogravimetric anal. [HMIM]HSO₄@silica and [HMBIM]HSO₄@silica have been successfully applied as promising replacements for conventional catalysts for alkane isomerization reactions at room temperature Isomerization of n-heptane and n-octane was achieved with both catalysts. In addition to promoting the isomerization of n-heptane and n-octane (a quintessential reaction for petroleum refineries), these immobilized catalysts are non-hazardous and save energy. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Quality Control of 1-Methylbenzimidazole).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Quality Control of 1-Methylbenzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem