Month: February 2023

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

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

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

Host-Guest Interactions between Candesartan and Its Prodrug Candesartan Cilexetil in Complex with 2-Hydroxypropyl-β-cyclodextrin: On the Biological Potency for Angiotensin II Antagonism was written by Ntountaniotis, Dimitrios;Andreadelis, Ioannis;Kellici, Tahsin F.;Karageorgos, Vlasios;Leonis, Georgios;Christodoulou, Eirini;Kiriakidi, Sofia;Becker-Baldus, Johanna;Stylos, Evgenios K.;Chatziathanasiadou, Maria V.;Chatzigiannis, Christos M.;Damalas, Dimitrios E.;Aksoydan, Busecan;Javornik, Uros;Valsami, Georgia;Glaubitz, Clemens;Durdagi, Serdar;Thomaidis, Nikolaos S.;Kolocouris, Antonios;Plavec, Janez;Tzakos, Andreas G.;Liapakis, George;Mavromoustakos, Thomas. And the article was included in Molecular Pharmaceutics in 2019.Computed Properties of C33H34N6O6 This article mentions the following:

Renin-angiotensin aldosterone system inhibitors are for a long time extensively used for the treatment of cardiovascular and renal diseases. AT1 receptor blockers (ARBs or sartans) act as antihypertensive drugs by blocking the octapeptide hormone Angiotensin II to stimulate AT1 receptors. The antihypertensive drug candesartan (CAN) is the active metabolite of candesartan cilexetil (Atacand, CC). Complexes of candesartan and candesartan cilexetil with 2-hydroxylpropyl-β-cyclodextrin (2-HP-β-CD) were characterized using high-resolution electrospray ionization mass spectrometry and solid state ¹³C cross-polarization/magic angle spinning NMR (CP/MAS NMR) spectroscopy. The ¹³C CP/MAS results showed broad peaks especially in the aromatic region, thus confirming the strong interactions between cyclodextrin and drugs. This exptl. evidence was in accordance with mol. dynamics simulations and quantum mech. calculations The synthesized and characterized complexes were evaluated biol. in vitro. It was shown that as a result of CAN’s complexation, CAN exerts higher antagonistic activity than CC. Therefore, a formulation of CC with 2-HP-β-CD is not indicated, while the formulation with CAN is promising and needs further investigation. This intriguing result is justified by the binding free energy calculations, which predicted efficient CC binding to 2-HP-β-CD, and thus, the mol.’s availability for release and action on the target is diminished. In contrast, CAN binding was not favored, and this may allow easy release for the drug to exert its bioactivity. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Computed Properties of C33H34N6O6).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) 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 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).Computed Properties of C33H34N6O6

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

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

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

Ionic liquids and cyclodextrin inclusion complexes: limitation of the affinity capillary electrophoresis technique was written by Mofaddel, Nadine;Fourmentin, Sophie;Guillen, Frederic;Landy, David;Gouhier, Geraldine. And the article was included in Analytical and Bioanalytical Chemistry in 2016.Application In Synthesis of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide This article mentions the following:

The state of the art of inclusion complex formation between cyclodextrins and ionic liquids is reported. Mechanisms, stoichiometries, and binding constants are summarized and classified by anion. We investigated the supramol. interactions between the β-cyclodextrin cavity and six ionic liquids based on 1-dodecyl-3-methylimidazolium by affinity capillary electrophoresis and compared the results with those obtained by isothermal titration calorimetry. We show that the presence of basic or acidic buffers leads to a metathesis reaction, underlining the limitation of the affinity capillary electrophoresis technique. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Application In Synthesis of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Application In Synthesis of 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17-a-estradiol late in life extends lifespan in aging UM-HET3 male mice; nicotinamide riboside and three other drugs do not affect lifespan in either sex was written by Harrison, David E.;Strong, Randy;Reifsnyder, Peter;Kumar, Navasuja;Fernandez, Elizabeth;Flurkey, Kevin;Javors, Martin A.;Lopez-Cruzan, Marisa;Macchiarini, Francesca;Nelson, James F.;Bitto, Alessandro;Sindler, Amy L.;Cortopassi, Gino;Kavanagh, Kylie;Leng, Lin;Bucala, Richard;Rosenthal, Nadia;Salmon, Adam;Stearns, Timothy M.;Bogue, Molly;Miller, Richard A.;Markewych, Adrian. And the article was included in Aging Cell in 2021.Reference of 145040-37-5 This article mentions the following:

In genetically heterogeneous mice produced by the CByB6F1 x C3D2F1 cross, the “non-feminizing” estrogen, 17-α-estradiol (17aE2), extended median male lifespan by 19% (p < 0.0001, log-rank test) and 11% (p = 0.007) when fed at 14.4 ppm starting at 16 and 20 mo, resp. 90th percentile lifespans were extended 7% (p = 0.004, Wang-Allison test) and 5% (p = 0.17). Body weights were reduced about 20% after starting the 17aE2 diets. Four other interventions were tested in males and females: nicotinamide riboside, candesartan cilexetil, geranylgeranylacetone, and MIF098. Despite some data suggesting that nicotinamide riboside would be effective, neither it nor the other three increased lifespans significantly at the doses tested. The 17aE2 results confirm and extend our original reports, with very similar results when started at 16 mo compared with mice started at 10 mo of age in a prior study. The consistently large lifespan benefit in males, even when treatment is started late in life, may provide information on sex-specific aspects of aging. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Reference of 145040-37-5).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) 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).Reference of 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Development and evaluation of rapidly disintegrating tablets of Candesartan was written by Ansari, Mohammad Pravej;Iqbal, Majid Md.;Saraswat, Rohit. And the article was included in World Journal of Pharmaceutical Research in 2019.Quality Control of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate This article mentions the following:

In the present work, Rapidly disintegrating tablets of Cadesartan cilexetil were designed with a view to enhance patient compliance by direct compression method. In the direct compression method, crospovidone, croscarmellose sodium, sodium starch glycolate as superdisintegrants were used along with Sweeteners and flavours were used to enhance the organoleptic properties of tablet. Tablets were prepared by direct compression technique. Directly compressible microcrystalline cellulose to enhance mouth feel. Prepared tablets were evaluated for thickness, uniformity of weight, hardness, friability, wetting time, in -vitro disintegration time, drug content and in vitro drug release. Short-term stability (40°C / 75% RH for 3 mo) and drug-excipient interaction study (IR spectroscopy) are also were studied. Disintegration time and drug release were taken as the basis to optimize the rapidly disintegrating tablet. All the formulations were evaluated for the influence of disintegrates and their concentrations on the characteristics of rapid disintegrating tablets mainly in terms of disintegration time and dissolution studies. The disintegration time of all formulation showed less than 37 s. Among the three superdisintegrants used, Crospovidon showed less disintegrating time followed by croscarmellose sodium and sodium starch gycolate. The relative efficiency of different superdisintegrants to improve the drug rate of tablets was in order, crospovidon > Croscarmellose sodium > sodium starch gycolate. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Quality Control of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) 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.Quality Control of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem