Month: January 2023

Oxa, Thia, Heterocycle, and Carborane Analogues of SQ109: Bacterial and Protozoal Cell Growth Inhibitors was written by Li, Kai;Wang, Yang;Yang, Gyongseon;Byun, Soo Young;Rao, Guodong;Shoen, Carolyn;Yang, Hongliang;Gulati, Anmol;Crick, Dean C.;Cynamon, Michael;Huang, Guozhong;Docampo, Roberto;No, Joo Hwan;Oldfield, Eric. And the article was included in ACS Infectious Diseases in 2015.Formula: C11H20N2 This article mentions the following:

The authors synthesized a library of 48 analogs of the Mycobacterium tuberculosis cell growth inhibitor SQ109 in which the ethylenediamine linker was replaced by oxa, thia, or heterocyclic species, and in some cases, the adamantyl group was replaced by a 1,2-carborane or the N-geranyl group by another hydrophobic species. Compounds were tested against M. tuberculosis (H37Rv and/or Erdman), Mycobacterium smegmatis, Bacillus subtilis, Escherichia coli, Saccharomyces cerevisiae, Trypanosoma brucei, and two human cell lines (human embryonic kidney, HEK293T, and the hepatocellular carcinoma, HepG2). The most potent activity was found against T. brucei, the causative agent of human African trypanosomiasis, and involved targeting of the mitochondrial membrane potential with 15 SQ109 analogs being more active than was SQ109 in cell growth inhibition, having IC₅₀ values as low as 12 nM (5.5 ng/mL) and a selectivity index of ∼300. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Formula: 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 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).Formula: C11H20N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and conversions of 2-formylbenzimidazoles was written by Dalgatov, D. D.. And the article was included in Sb. Aspirantskikh Rabot, Dagestansk. Univ., Estestv, i Fiz.-Mat. Nauk, Makhachkala in 1964.Recommanded Product: 3012-80-4 This article mentions the following:

Methods for synthesis of 2-formylbenzimidazoles (I) and the N-Me (II) and N-Ph (III) derivatives of I were studied. II was condensed with Me ketones and PhCH₂NO₂ (IV) and I and II were condensed with cyclohexanone (V). 1,2-Bis(2-benzimidazolyl)ethylene glycol (2.94 g.) was dissolved in 100 ml. N HCl, 2.3 g. KIO₄ added, the solution kept 2 days at 20°, and 10% Na₂CO₃ added to alkalinity to yield 93% I, m. 235° (alc.) (decomposition). I (1.46 g.), 7 ml. V, and 7 ml. MeOH was heated at 100°, 5-6 drops 20% KOH added, and the mixture cooled after 10-15 min. to yield 75% the 2-(2-benzimidazolylmethylene) derivative of V, sublimes 175-80° (MeOH). KOH (5.6 g.) and 13.2 g. 2-methylbenzimidazole (VI) in 50 ml. alc. was boiled, 17.2 g. PhSO₃Me added after 1 hr., the mixture heated 2 hrs. and filtered, and the filtrate evaporated to give 10.3 g. l-Me derivative (VIa) of VI, m. 112° (H₂O). Oxidation of VIa with SeO₂ in PhMe at 95° yielded 40% II. 1-Methyl-2-(hydroxymethyl)benzimidazole (1.6 g.) was dissolved in 50 ml. 2N H₂SO₄, 0.05 g. AgNO₃ added, the mixture heated to 70° K₂S₂O₈ added after 4 hrs., the mixture filtered, and the filtrate neutralized with Na₂CO₃ solution to yield 0.4 g. II, m. 110°. II (1.6 g.) and 1.49 g. isonicotinic hydrazide in 8 ml. MeOH was boiled 20 min. to yield 2 g. isonicotinoyl hydrazone of II, m. 200-3° (MeOH). 2-(Hydroxymethyl)benzimidazole (VII) (14.8 g.), 21.2 g. unsaturated leukotrone O, and a concentrated solution of 4 g. NaOH was heated 4 hrs., and Me₂NPh steam distilled to yield 12 g. 1-PhCH₂ derivative of VII, m. 186.5-87° (alc.). To 1.6 g. II and 1.99 g. p-bromoacetophenone (VIII) in 3 ml. MeOH was added 2-3 drops 5% KOH to yield 70% 2-[β-(p-bromobenzoyl)vinyl]-1-methylbenzimidazole, m. 159-60° (alc.). II (1.6 g.) and 3.98 g. VIII were dissolved in 10 ml. hot MeOH, 2 ml. 20% KOH added, and the mixture boiled 1 hr. to yield 74% 1-methyl-2-bis(p-bromo-phenacylmethyl)benzimidazole, m. 186.5-87° (MeOH). Analogously was obtained 2-(β-tolylvinyl)-1-methylbenzimidazole, m. 134° (alc.). II (1.6 g.) and 0.98 g. IV in 5 ml. MeOH and 3 drops 10% KOH was boiled 0.5 hr. to yield 1.7 g. 2-(1-methyl-2-benzimidazolylmethylene) derivative of V, m. 237° (CHCl₃). To 1.37 g. IV in 8 ml. alc. was added 1 g. NaOH in 8 ml. H₂O and in portions 1.6 g. of a solution of II in 10 ml. alc. and after 5 hrs. the mixture neutralized with 1:1 aqueous HCl to yield 73% 2-(β-nitro- α-hydroxy-β-phenylethyl)-1-methylbenzimidazole, m. 162-3° (decomposition) (alc.-Me₂CO). To 20.8 g. 2-methyl-1-phenylbenzimidazole in 200 ml. anhydrous PhMe at 95° was added 11.1 g. SeO₂ over 4 hrs., the mixture heated 2 hrs., the PhMe layer separated and steam distilled, and the residue treated with CHCl₃ to yield 35% III (oil); dinitrophenylhydrazone m. 260-1°; semi-carbazone m. 255-6°. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Recommanded Product: 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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. 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. Recommanded Product: 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Enantioselective Hydrogenation of Imidazo[1,2-a]pyridines was written by Schlepphorst, Christoph;Wiesenfeldt, Mario P.;Glorius, Frank. And the article was included in Chemistry – A European Journal in 2018.Reference of 69214-09-1 This article mentions the following:

The enantioselective synthesis of tetrahydroimidazo[1,2-a]pyridines by direct hydrogenation was achieved using a ruthenium/N-heterocyclic carbene (NHC) catalyst. The reaction forgoes the need for protecting or activating groups, proceeds with complete regioselectivity, good to excellent yields, enantiomeric ratios of up to 98:2, and tolerates a broad range of functional groups [e.g., I → II (95.5:4.5 e.r., 99% isolated yield)]. 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridines, which are found in numerous bioactive mols., were directly obtained by this method, and its applicability was demonstrated by the (formal) synthesis of several functional mols. In the experiment, the researchers used many compounds, for example, 5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1Reference of 69214-09-1).

5-Bromoimidazo[1,2-a]pyridine (cas: 69214-09-1) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 69214-09-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

New reactive ionic liquids as carriers in polymer inclusion membranes for transport and separation of Cd(II), Cu(II), Pb(II), and Zn(II) ions from chloride aqueous solutions was written by Szczepanski, Piotr;Guo, Haopeng;Dzieszkowski, Krzysztof;Rafinski, Zbigniew;Wolan, Andrzej;Fatyeyeva, Kateryna;Kujawa, Joanna;Kujawski, Wojciech. And the article was included in Journal of Membrane Science in 2021.Application In Synthesis of 1-Octyl-1H-imidazole This article mentions the following:

Three new reactive ionic liquids (RILs) based on the imidazole derivatives were synthesized and used as carriers in polymer inclusion membranes (PIMs) composed of cellulose triacetate (CTA) as a polymer matrix and o-nitrophenyl octyl ether (NPOE) as a plasticizer. The effect of alkyl chain length (C1, C4, and C8) in the imidazolium cation of RILs on the transport and separation properties was evaluated. From among three synthesized RILs only the RIL with the longest alkyl chain (RILC8_Br) can be successfully applied as the carrier for Cd(II) removal from multicomponent aqueous chloride solution containing also Cu(II), Pb(II), and Zn(II) ions. The effects of the stripping phase composition, HCl concentration in the feed solution, and the carrier content in the membrane on the separation performance and transport effectiveness were studied. The results indicate that the RILC8_Br ionic liquid enables selective transport of Cd(II) ions and their active concentration in the stripping solution with the fluxes reaching a value of 2.7 x 10^-10 mol/cm²s. In the investigated feed solution concentration range, the selectivity order was found to be Cd(II) > Zn(II) > Pb(II) ≫ Cu(II) and it was independent of the exptl. conditions. For a description of the transport kinetics a model similar to the first-order reversible reaction equations was applied and its applicability was proved. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Application In Synthesis of 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Application In Synthesis of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Photoexcitation dynamics of p-nitroaniline and N,N-dimethyl-p-nitroaniline in 1-alkyl-3-methylimidazolium-cation based ionic liquids with different alkyl-chain lengths was written by Kimura, Y.;Ibaraki, S.;Hirano, R.;Sugita, Y.;Yasaka, Y.;Ueno, M.. And the article was included in Physical Chemistry Chemical Physics in 2017.Formula: C18H31F6N3O4S2 This article mentions the following:

Photoexcitation dynamics of p-nitroaniline (pNA) and N,N-dimethyl-p-nitroaniline (DMpNA) in 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([C_nmim][NTf₂]) with different alkyl chain lengths (from C₂ to C₁₂) was investigated using transient absorption spectroscopy. The internal conversion rate from the excited state to the ground state was estimated from bleach recovery around the ground state absorption center, and the successive vibrational cooling rate in the ground state was estimated from the decay of the hot band observed at the red-edge of ground state absorption. The internal conversion rate slightly decreased with an increase in the alkyl-chain length of the cation, while the dependence of DMpNA was more significant than that of pNA. The extent of change was correlated with the change of the reaction free energy and solvent reorganization energy estimated from the absorption spectrum assuming that the internal conversion process is modeled by a back-electron-transfer process. The vibrational cooling rate estimated from the decay of hot-band absorption slightly decreased with an increase in the alkyl-chain length of the cation for both solutes. The hot-band decay of pNA was about 1.5-times faster than that of DMpNA, irresp. of the alkyl-chain length. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Formula: C18H31F6N3O4S2).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Formula: C18H31F6N3O4S2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sustainable spectrophotometric determination of antihypertensive medicines reducing COVID-19 risk via paired wavelength data processing technique – Assessment of purity, greenness and whiteness was written by El-Hanboushy, Sara;Marzouk, Hoda M.;Fayez, Yasmin M.;Abdelkawy, Mohamed;Lotfy, Hayam M.. And the article was included in Sustainable Chemistry and Pharmacy in 2022.Recommanded Product: 145040-37-5 This article mentions the following:

Recent studies have reported that using certain antihypertensive therapies such as angiotensin II receptor blockers (ARBs) is associated with mitigation of fatal outcomes and enhancing clin. features of patients having hypertension during coronavirus pandemic. Thus, in the current work an innovative, effective, white and sustainable spectrophotometric technique called paired wavelength data processing technique (PWDPT) was developed for evaluation of recommended antihypertensive combination therapies incorporating candesartan cilexetil (CAN) and hydrochlorothiazide (HCT). This technique included three methods, namely, absorbance resolution (AR), amplitude resolution (PR) and ratio extraction (RE). Linearity ranges were (5.0 μg/mL – 50.0 μg/mL) and (2.0 μg/mL – 24.0 μg/mL) for CAN and HCT, resp. Validation and confirmation of all suggested methods were conducted in accordance with ICH guidelines, producing satisfactory results within the accepted limits. Statistical comparison was achieved between the attained results from suggested methods and those attained from official methods, in which insignificant difference was existed. The suggested methods were successfully employed for identification of the studied drugs as well as determination of their spectral recognition and evaluation of the purity in their combined formulations. The proposed methods followed the principles of green anal. chem., where their greenness was evaluated and compared with the official potentiometric and HPLC methods via using four tools, namely, National Environmental Methods Index (NEMI), the Anal. Eco-Scale, the Green Anal. Procedure Index (GAPI) and Anal. greenness metric (AGREE) which affirmed the eco-friendly nature of the proposed methods. Moreover, studying the whiteness features was performed using the recently introduced RGB12 model. The acceptable results along with the sustainability, simplicity, affordability and low-cost of the proposed methods encourages their utilization in the quality control laboratories 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: 145040-37-5Recommanded Product: 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Recommanded Product: 145040-37-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Terminal anion induced zinc(II) mononuclear complexes trans-to-cis isomerization regulate photoluminescence properties and its solution behavior was written by Li, Shixiong;Liu, Lingmei;Deng, Yan;Huang, Yuanhao;Chen, YuFeng;Liao, Beiling. And the article was included in Polyhedron in 2019.Reference of 3012-80-4 This article mentions the following:

The organic ligand 1-methyl-1H-benzo[d]imidazole-2-carbaldehyde (L’) was used to react with ZnX₂ (X = Cl and Br) under solvothermal conditions to obtain [Zn(L)₂(X)₂] (1, X = Cl; 2, X = Br). The ligand of L’ transforms into 1-methyl-1H-benzo[d]imidazole (L). The structures anal. shows that the L’ ligands of complex 1 and 2 coordinate in different way, which results different shapes in every structure. They are trans and cis isomers of Zn(II) mononuclear complexes induced by terminal anions. These also lead to the difference of weak interaction of complexes, thus affecting the mode of connection. Also, the electrospray ionization mass spectrometry (ESI-MS) data show that the main mol. fragment was [Zn(L)₂(X)]⁺ under the condition of 0 eV voltage. So those two complexes were relatively stable in CH₃CN. The single crystals of complex 1 showed blue green light, but complex 2 showed very obvious blue and white light under UV lamp, this difference may be due to the ion radius of coordination halogen. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Reference of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) 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.Reference of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Theoretical investigation of imidazolium based ionic liquid/alcohol mixture: a molecular dynamic simulation was written by Jahangiri, S.;Taghikhani, M.;Behnejad, H.;Ahmadi, S. J.. And the article was included in Molecular Physics in 2008.COA of Formula: C7H13ClN2 This article mentions the following:

In this work, mol. dynamic simulation of the mixture of imidazolium based ionic liquids with alcs. is implemented in order to investigate mixing excess properties and some structural and phys. properties of the mixture Excess volumes and enthalpies are evaluated for 11 different mole fractions of ionic liquids at each 0.1, in the range of 0 to 1. Radial distribution function, cohesive energy d., potential of mean force, solvation energy, and diffusion coefficient are reported and analyzed. The effects of the cationic alkyl chain length, in comparison with changes of the anions, on these properties are reported. Results reveal that the methanol mol. participates with its hydrophilic characteristics in the mixing process and tends to aggregate around anion part of the ionic liquids, especially in the case of Cl. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8COA of Formula: C7H13ClN2).

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 derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.COA of Formula: C7H13ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Inhibition of dealkylation of 7-methoxy and 7-ethoxycoumarin in rat liver microsomes by disulfiram, 2-n-octyl benzimidazole, chloramphenicol and propranolol was written by Fry, Jeffrey R.. And the article was included in IRCS Medical Science in 1984.Electric Literature of C15H22N2 This article mentions the following:

Both the 7-methoxy- [72750-64-2] and 7-ethoxycoumarin dealkylase  [42613-26-3] activities of rat liver microsomes were equally inhibited by cytochrome P 450  [9035-51-2] antagonists with the following order of potency: disulfiram  [97-77-8] > 2-n-octyl benzimidazole  [13060-24-7] > chloramphenicol  [56-75-7] > propranolol  [525-66-6]. Thus, whereas all 4 compounds are effective inhibitors of cytochrome P 450-dependent monooxygenase  [9038-14-6] activity, they do not show any selectivity for the constitutive forms of cytochrome P 450 involved in the dealkylation of the 7-alkoxycoumarins. In the experiment, the researchers used many compounds, for example, 2-Octylbenzimidazole (cas: 13060-24-7Electric Literature of C15H22N2).

2-Octylbenzimidazole (cas: 13060-24-7) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Electric Literature of C15H22N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Tin(II) chloride-catalyzed synthesis of 2-alkylbenzimidazole was written by Ho, Son Lam;Tran, Hong Trang;Le, Thi Hoa;Nguyen, Duc Hai;Nguyen, Thi Thanh Xuan. And the article was included in Tap Chi Hoa Hoc in 2004.Computed Properties of C15H22N2 This article mentions the following:

2-Substituted benzimidazoles have been synthesized by condensation of o-phenylenediamine with carboxylic acids (C₂-C₉) using SnCl₂ as catalyst. The reaction mixture was heated in dioxane in stainless steel autoclave for 10 h with stirring at 180°C. In the experiment, the researchers used many compounds, for example, 2-Octylbenzimidazole (cas: 13060-24-7Computed Properties of C15H22N2).

2-Octylbenzimidazole (cas: 13060-24-7) 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. 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. Computed Properties of C15H22N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem