Month: February 2023

Synthesis of heteroxanthine from a derivative of imidazole was written by Sarasin, J.;Wegmann, E.. And the article was included in Helvetica Chimica Acta in 1924.Application In Synthesis of 1-Methyl-4-nitroimidazole This article mentions the following:

S. and W. describe a new synthesis of 7-methylxanthine from an imidazole derivative, by closing the pyrimidine ring, an operation which has not been previously effected. 1-Methyl-4-nitro-5-chloroimidazole (I) is obtained in theoretical yield from 1-methyl-5-chloroimidazole (b. 200°) (II) by dissolving in dilute HNO₃ to form the nitrate, treating the latter with cold concentrated H₂SO₄, heating the mixture on the water bath for 2 hrs., and pouring the product on ice; it m. 147-8°, and is insoluble in acids and dilute alkalies. The isomeric 1-methyl-5-nitro-4-chloroimidazole (III), obtained by the same method from 1-methyl-4-chloroimidazole; m. 77-8°. I and III are reduced at 0° by Sn and HCl to the corresponding methylchloroaminoimidazoles which were not obtained in the pure state. I heated for several hrs. on the H₂O bath in EtOH with 2 mols. KCN and 0.1 mol. KI yields 85% 1-methyl-4-nitro-5-cyanoimidazole (IV), m. 141-2°, insoluble in acids and dilute alkalies. 1-Methyl-4-nitroimidazole-5-carboxamide (V), obtained in 90% yield when IV is heated for 2 hrs. on the H₂O bath with 8 times its weight of concentrated H₂SO₄ and the product is poured on ice, m. 257-8° (decomposes), insoluble in acids and alkalies, saponified with great difficulty; a small amount of the acid (VI) is obtained by prolonged action of concentrated HCl. VI m. 160° with evolution of CO₂ and formation of 1-methyl-4-nitroimidazole (VII), m. 133-40°, which is also obtained by heating V in a sealed tube at 120° with HCl. Reduction of VII by Sn and HCl at 0° and hydrolysis of the product by heating under pressure with HCl, gives NH₄Cl and sarcosine-HCl, m. 168-9°; this reaction establishes the constitution of II and VII. V is reduced at 0° by Sn and HCl to the corresponding amine, 1-methyl-4-aminoimidazole-5-carboxamide (VIII), m. 184-5°, decomposed when heated with water or dilute alkalies with evolution of NH₃; HCl salt, m. 214-5°. 7-Methylxanthine (heteroxanthine) obtained in 38% yield by heating 0.4 g. of VIII for 8 hrs. in a sealed tube at 160-70° with an equal weight of CO(OEt)₂, m. 380° (browning and evolution of gas). A mixture of the substance with heteroxanthine prepared from theobromine melts at the same temperature The murexide reaction is given with KClO₃ and HCl. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application In Synthesis of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.Application In Synthesis of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The synthesis of heterocycles via addition-elimination reactions of 4- and 5-aminoimidazoles was written by Al-Shaar, Adnan H. M.;Chambers, Robert K.;Gilmour, David W.;Lythgoe, David J.;McClenaghan, Ian;Ramsden, Christopher A.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1992.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

4-Aminoimidazoles, e.g. I (R = H, R¹ = H, Me, CH₂Ph; R² = H, Me, Et, CHMe₂), undergo addition elimination reactions with electrophilic reagents to give exclusively N-adducts, which are useful intermediates for further synthetic transformations to novel heterocyclic systems. Thus, di-Et ethoxymethylenemalonate (II) and 4-amino-1-benzylimidazole give the adduct I [R = HC:C(CO₂Et)₂, R¹ = CH₂Ph, R² = H], and subsequent acid-catalyzed cyclization gives the imidazo[4,5-b]pyridine III and a heterocyclic mesomeric betaine, which undergoes 1,3-dipolar cycloaddition with di-Me acetylenedicarboxylate to give two products. When the 2-alkyl-4-aminoimidazoles I (R = R¹ = H, R² = Me, Et, CHMe₂) are generated in situ in the presence of II, 5,5′-diimidazoles are significant products; a mechanism for this novel transformation is proposed. 4-Amino-3-cyanoimidazo[1,5-a]pyrimidines IV (R = H, Me) are formed by cyclization of the N-adduct of I (R = R¹ = R² = H) and CR³(OEt):C(CN)₂ (R³ = H, Me). The use of X:NCN [V; X = CH(OEt), CMe(OEt), C(SMe)₂] leads to novel 4-aminoimidazo[1,5-a]-1,3,5-triazine derivatives VI (R¹ = H, Me, SMe; R² = H, Me), whose chem. reactions with both electrophilic and nucleophilic reagents are reported. 5-Aminoimidazoles, e.g., VII (R = H, R¹ = Me, CH₂CH₂OH; R² = Me, CHMe₂), undergo addition-elimination reactions with the electrophilic reagents, e.g. II and V, to give N-adducts and/or C-adducts, depending upon the structure of the reagent. These stable addition-elimination products are usually obtained in good yield and are useful intermediates for further synthesis. Reaction of the amines VII with II gives mainly N-adducts VII [R = HC:C(CO₂Et)₂], which can be cyclized using phosphoryl chloride to give the versatile 7-chloroimidazo[4,5-b]pyridines VIII. With ethoxymethylenemalononitrile, the amines VII give C-adducts, which undergo thermal cyclization to give 5-amino-6-cyanoimidazo[4,5-b]pyridines IX, which are further transformed into novel heterocyclic systems, including the tricyclic imidazo[4′,5′:5,6]pyrido[2,3-d]pyrimidines X (R = H, Ph) and XI (R = H, Bu, CH₂Ph, CH₂CH₂OH). Cyclization of the adducts obtained using V provides new synthetic route to aminopurine derivatives, e.g. XII (R³ = H, NH₂, SMe), and hypoxanthines. The preference of electrophilic reagents for N– or C-addition to VII is rationalized using Frontier MO theory. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ionic liquids as coagents for sulfur vulcanization of butadiene-styrene elastomer filled with carbon black was written by Maciejewska, Magdalena;Zaborski, Marian. And the article was included in Polymer Bulletin (Heidelberg, Germany) in 2018.Application of 404001-48-5 This article mentions the following:

The aim of this work was to study the activity of several alkylimidazolium salts of bis(trifluoromethylsulfonyl)imides to obtain a very fast vulcanization of the butadiene-styrene (SBR) elastomer. Ionic liquids (ILs) such as alkylimidazolium salts with ethyl-, propyl-, butyl-, hexyl-, decyl-, dodecyl-, and hexadecyl chains in the cation together with nanosized zinc oxide are used to develop elastomer composites with very short vulcanization time and a reduced amount of vulcanization activator. In this article, we discuss the effect of the ILs with respect to the length of alkyl chain in their cation on the vulcanization kinetics of rubber compounds The influence of ILs on the crosslink d. as well as the mech. properties of the vulcanizates and their resistance to thermo-oxidative and UV aging were also studied. ILs resulted in a shortened optimal vulcanization time and reduced the onset vulcanization temperature compared to zinc oxide containing rubber compound This is very important from a technol. point of view. A considerable increase in the crosslink d. of vulcanizates was also observed 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 of 404001-48-5).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Application of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

CNDO/S method interpretation of ultraviolet spectra of 4-nitro and 5-nitroimidazoles was written by Crozet, M. P.;Vanelle, P.;Bouscasse, L.;Avignon, T.. And the article was included in Spectroscopy Letters in 1986.Safety of 1-Methyl-4-nitroimidazole This article mentions the following:

The UV spectra of several nitroimidazoles are reported. These exptl. results are interpreted using CNDO/S method (CNDO for Spectroscopy). Observed transitions are π → π^* type transitions. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Safety of 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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.Safety of 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Efficient synthesis of styrene carbonate from CO₂ and styrene oxide using zinc catalysts immobilized on soluble imidazolium-styrene copolymers was written by Qiao, Kun;Ono, Fumitaka;Bao, Quanxi;Tomida, Daisuke;Yokoyama, Chiaki. And the article was included in Journal of Molecular Catalysis A: Chemical in 2009.HPLC of Formula: 915358-85-9 This article mentions the following:

Preparation of zinc catalysts (Zn/PS-IL[X], X = Br^–, Cl^–, BF₄ ^–, and PF₆ ^–) supported on imidazolium-styrene copolymers, as well as their catalytic use for the solvent-free synthesis of styrene carbonate from CO₂ and styrene oxide, are described. Among the catalysts examined, Zn/PS-IL[Br] was proved to be the most efficient. When used in a homogeneous system during the reaction process, Zn/PS-IL[Br] gave a 97.5% yield of product with a TOF value that can be up to about 3800 h^-1. Due to its immiscibility with ethanol, Zn/PS-IL[Br] can be separated like a heterogeneous catalyst through solvent precipitation, and reused at least three times for the reaction without significant loss of activity. In the experiment, the researchers used many compounds, for example, 1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9HPLC of Formula: 915358-85-9).

1-Butyl-3-vinyl-1H-imidazol-3-ium hexafluorophosphate(V) (cas: 915358-85-9) 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 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).HPLC of Formula: 915358-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis of polysiloxane random copolymers that contain quaternized imidazolium moieties was written by Ichikawa, Tsukasa;Nemoto, Nobukalsu. And the article was included in Kobunshi Ronbunshu in 2016.Electric Literature of C11H20N2 This article mentions the following:

Polysiloxane random copolymers that contain quaternized imidazolium salts ([PImn]Cl) (n is the number of methylene groups) were obtained by the quaternization reaction of poly[dimethylsiloxane-ran-(3-chloropropylmethylsiloxane)] (P1) with imidazole derivatives having different lengths of alkyl chains (Imn) at the 1-position. The introduction ratio of imidazolium salts into P1 was estimated to be from 93 to 100 mol % from ¹H NMR anal. The glass transition temperatures (T_gs) of [PImn]Cls were determined by differential scanning calorimetry (DSC). Of all the samples. [Plm5]Cl and [Plm6]|Cl had the lowest T_g of 14°C which is 12-15 K lower than the T_g of polysiloxane homopolymer having quaternized imidazolium salts without polydimethylsiloxane units. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Electric Literature of C11H20N2).

1-Octyl-1H-imidazole (cas: 21252-69-7) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Electric Literature of C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Comparison of the antihypertensive activity of Telmisartan versus valsartan in queen alia heart institute/royal medical services was written by Alzayaat, Hadeel H.;Abu-Roman, Wafa M.;Al-Abbadi, Nawal H.;Al-Maseeb, Ma’aali M.;Jibreen, Abeer A.. And the article was included in Scholars Academic Journal of Pharmacy in 2018.COA of Formula: C33H34N6O6 This article mentions the following:

Hypertension is a major risk factor for stroke, myocardial infarction, vascular disease, and chronic kidney disease. The goal of antihypertensive therapy is to maintain blood pressures of < 140/90 mmHg for most people. All international guidelines for the management of hypertension recommend angiotensin receptor blockers (ARBs) as an initial or add-on antihypertensive therapy. The ARBs are very well tolerated as monotherapy as well as in combination with other anti-hypertensive medications that improve adherence to therapy and have become a mainstay in the treatment of stage 1 and 2 hypertension. The 8 available ARBs have variable clin. efficacy when used for control of hypertension. Assessment of the efficacy and safety of Telmisartan (80 mg once daily) vs. valsartan (160 mg once daily) for the management of blood pressure (BP) in patients with essential hypertension. A cross sectional retrospective single center, parallel-group study. Patients will be recruited from Queen Alia Heart Institute. Data will be gathered by reviewing the medical records. Baseline characteristics were not significantly different between the two study groups. After 12 wk, BP had fallen to a greater extent in the Telmisartan group compared to Valsartan group in terms of mean reductions in the systolic and diastolic BP of 126.2/80.4 (Adjusted change from baseline- 26.8/-20.9) and 133.3/ 86.8 mm Hg (Adjusted change from baseline–18 /-12.7) (p<0.0021). In Stage 2 hypertensive patients once daily Telmisartan 80 mg provides significantly greater BP lowering compared to Valsartan 160 mg. 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: 145040-37-5COA of Formula: 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. 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 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).COA of Formula: C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Pretreatment of yellow pine in an acidic ionic liquid: Extraction of hemicellulose and lignin to facilitate enzymatic digestion was written by Cox, Blair J.;Ekerdt, John G.. And the article was included in Bioresource Technology in 2013.Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride This article mentions the following:

The acidic ionic liquid 1-H-3-methylimidazolium chloride can effectively pretreat yellow pine wood chips under mild conditions for enzymic saccharification. Wood samples were treated at temperatures between 110 and 150 °C for up to 5 h in the ionic liquid and three fractions collected; a cellulose rich fraction, lignin, and an aqueous fraction. This treatment caused the hemicellulose and the lignin to be degraded and dissolved from the cell walls of the pine wood. The lignin was depolymerized and subsequently dissolved in the ionic liquid This process occurred more quickly at higher temperatures, although at the highest temperatures tested, significant cellulose degradation also occurred. The cellulose rich fraction was saccharified using cellulase from Trichoderma viride, with longer pretreatment times at 130 °C resulting in higher glucose yields. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) 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 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).Recommanded Product: 1-Methyl-1H-imidazol-3-ium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Extended dissolution studies of cellulose in imidazolium based ionic liquids was written by Vitz, Juergen;Erdmenger, Tina;Haensch, Claudia;Schubert, Ulrich S.. And the article was included in Green Chemistry in 2009.Category: imidazoles-derivatives This article mentions the following:

Ionic liquids (ILs) have become advantageous solvents for the dissolution and homogeneous processing of cellulose in recent years. However, despite significant efforts, only a few ILs are known for their capability to efficiently dissolve cellulose. In order to overcome this limitation, we screened a wide range of potentially suitable ILs. From our studies, some remarkable results were obtained, for example, an odd-even effect was found for different alkyl side-chain lengths of the imidazolium chlorides which could not be observed for the bromides. Furthermore, 1-ethyl-3-methylimidazolium di-Et phosphate was found to be best suitable for the dissolution of cellulose; dissolution under microwave irradiation resulted in almost no color change. No degradation of cellulose could be observed In addition, 1-ethyl-3-methylimidazolium di-Et phosphate has a low m.p. which makes the viscosity of the cellulose solution lower and, thus, easier to handle. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Category: imidazoles-derivatives).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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. Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Low-melting, low-viscous, hydrophobic ionic liquids: 1-alkyl(alkyl ether)-3-methylimidazolium perfluoroalkyltrifluoroborate was written by Zhou, Zhi-Bin;Matsumoto, Hajime;Tatsumi, Kuniaki. And the article was included in Chemistry – A European Journal in 2004.Reference of 79917-89-8 This article mentions the following:

Twenty two hydrophobic ionic liquids, 1-alkyl(alkyl ether)-3-methylimidazolium ([C_mmim]⁺ or [C_mO_nmim]⁺; where C_m is 1-alkyl, C_m = nC_mH_2m+1, m = 1-4 and 6; C_mO_n is 1-alkyl ether, C₂O₁ = CH₃OCH₂, C₃O₁ = CH₃OCH₂CH₂, and C₅O₂ = CH₃(OCH₂CH₂)₂) perfluoroalkyltrifluoroborate ([R_FBF₃]^–, R_F = CF₃, C₂F₅, nC₃F₇, nC₄F₉), were prepared and characterized. Some of the important physicochem. properties of these salts including m.p., glass transition, viscosity, d., ionic conductivity, thermal and electrochem. stability, were determined and were compared with those of the reported [BF₄]^–-based ones. The influence of the structure variation in the imidazolium cation and the perfluoroalkyltrifluoroborate ([R_FBF₃]^–) anion on the above physicochem. properties is discussed. The key features of these new salts are their low m.ps. (-42 to 35°) or extremely low glass transition (between -87 and -117°) without melting, and considerably low viscosities (26-77 cP at 25°). In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Reference of 79917-89-8).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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 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 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem