Category: imidazoles-derivatives

Chemistry of fairy ring. Clarification of the identity of the fairy and application to agriculture was written by Choi, Jae-Hoon;Kawagishi, Hirokazu. And the article was included in Kagaku to Seibutsu in 2011.Application In Synthesis of 1H-Imidazole-4-carboxamide This article mentions the following:

A review on the “fairy ring” (fungus-stimulated plant growth) on lawns; enhancement of grass growth by Lepista sordida; identification of 2-azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) as a pos. and neg. growth regulator for grasses in the culture medium of L. sordida; stimulation of plant growth by AHX; increased expression of GST, BBI, and OsTIP2;1 genes in rice by AHX treatment; and increase of the yields of rice by AHX and ICA. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Application In Synthesis of 1H-Imidazole-4-carboxamide).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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 1H-Imidazole-4-carboxamide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Chemiluminescence intensities of substituted lophines was written by Philbrook, George E.;Maxwell, Michael A.. And the article was included in Tetrahedron Letters in 1964.Reference of 5496-35-5 This article mentions the following:

The intensities of the chemiluminescence and the ir and uv absorption spectra were investigated for lophine, 4-dimethylamino-, 4-acetamino, 4-methoxy, 3,4-dimethoxy, 3,4-diethoxy, 4-methyl, 4-isopropyl-, 4-chloro-, 4-fluoro-, 4-bromo-, 3-nitro, 4-nitro-, 4-phenoxy-, and 4-carboxylophine (substituents in the 2 position on the ring) in 70% Me2SO in 30% N NaOH. The curves, log I/I0 = f(σ) (Hammett) were plotted; I depended linearly on the lophine concentration and could be increased by H2O2. Spontaneous evaporation and spontaneous absorption were not found. All the chemiluminescence processes investigated were explained by the fact that, at times, the same mol. fragment was formed. In the experiment, the researchers used many compounds, for example, 4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5Reference of 5496-35-5).

4-(4,5-Diphenyl-1H-imidazol-2-yl)benzoic acid (cas: 5496-35-5) 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.Reference of 5496-35-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sequence-specific protection of plasmid DNA from restriction endonuclease hydrolysis by pyrrole-imidazole-cyclopropapyrroloindole conjugates was written by Fujimoto, Kazuhisa;Iida, Hirokazu;Kawakami, Masako;Bando, Toshikazu;Tao, Zhi-Fu;Sugiyama, Hiroshi. And the article was included in Nucleic Acids Research in 2002.Category: imidazoles-derivatives This article mentions the following:

The pyrrole-imidazole (Py-Im) triamide-cyclopropa pyrroloindole (CPI) conjugates ImPyImLDu86 (7) and ImImPyLDu86 (14) were synthesized and their alkylating activities and inhibitory effects on DNA hydrolysis by restriction endonucleases were examined Sequencing gel anal. demonstrated that conjugates 7 and 14 specifically alkylated DNA at 5′-CGCGCG-3′ and 5′-PyGGCCPu-3′, resp. Agarose gel electrophoresis indicated that incubation of a supercoiled plasmid, pSPORT I (4109 bp), with conjugate 7 effectively inhibited its hydrolysis by BssHII (5′-GCGCGC-3′), whereas conjugate 14 had no effect on this hydrolysis. These results suggest that conjugate 7 sequence-specifically inhibits the hydrolysis of DNA by BssHII. Sequence-specific alkylation by the Py-Im triamide-CPI conjugates was further confirmed by inhibition of the Eco52I (5′-CGGCCG-3′) hydrolysis of conjugate 14-treated pQBI PGK (5387 bp). In clear contrast, hydrolysis of pQB1 PGK by DraI (3′-TTTAAA-3′) was not inhibited by 5 μM conjugate 14. That ImImPy did not inhibit the hydrolysis of pQB1 PGK indicates that covalent bond formation is necessary for inhibition. A similar experiment, using linear pQBI PGK, achieved the same extent of protection of the DNA with approx. half the concentration of conjugate 14 as was required to protect supercoiled DNA from hydrolysis. In the experiment, the researchers used many compounds, for example, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9Category: imidazoles-derivatives).

Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (cas: 109012-23-9) 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).Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

ROS-mediated autophagy through the AMPK signaling pathway protects INS-1 cells from human islet amyloid polypeptide-induced cytotoxicity was written by Xia, Guanghao;Zhu, Tiehong;Li, Xiaotong;Jin, Yujing;Zhou, Jing;Xiao, Jinfeng. And the article was included in Molecular Medicine Reports in 2018.Recommanded Product: 1H-Imidazole-4-carboxamide This article mentions the following:

Oligomerization of human islet amyloid polypeptide (hIAPP) is toxic and contributes to progressive reduction of β cell mass in patients with type 2 diabetes mellitus. Therefore, the present study investigated the underlying mol. mechanism and regulatory pathway of hIAPP-induced autophagy. Transmission electron microscopy was used to observe the number of autophagosome in cells. Cell viability was determined by an MTT test. A 2′,7′-dichlorofluorescin diacetate assay was used to measure the relative levels of reactive ROS. Western blotting was used to detect expression of adenosine monophosphate-activated protein kinase (AMPK) and autophagic markers p62 and microtubule associated protein 1 light chain 3. The results demonstrated that hIAPP induces autophagy through ROS-mediated AMPK signaling pathway in INS-1 cells. Upregulation of autophagy by AMPK activator 5-aminoimidazole-4-carboxamide1-β-D-ribofurano side decreased ROS and malondialdehyde generation, whereas inhibition of autophagy by 3-methyladenine and AMPK inhibitor compound C aggravated hIAPP-induced oxidative stress and toxicity in INS-1 cells. Taken together, the present study suggested that hIAPP induces autophagy via a ROS-mediated AMPK signaling pathway. Furthermore, autophagy serves as a cell-protective mechanism against hIAPP-induced toxicity and chem. promotion of autophagy through AMPK signaling pathway attenuates hIAPP induced cytotoxicity and oxidative stress in INS-1 cells. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Recommanded Product: 1H-Imidazole-4-carboxamide).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) 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.Recommanded Product: 1H-Imidazole-4-carboxamide

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Analysis of the heterogeneous dynamics of imidazolium-based [Tf₂N^–] ionic liquids using molecular simulation was written by Androulaki, Eleni;Vergadou, Niki;Economou, Ioannis G.. And the article was included in Molecular Physics in 2014.Category: imidazoles-derivatives This article mentions the following:

The complex dynamic behavior of the imidazolium-based ionic liquids [C_nmim⁺][Tf₂N^–], n = 4, 8, 12 is examined at various temperatures and at atm. pressure using mol. dynamics simulation. An existing all-atom force field is further optimized in order to attain reasonable agreement with exptl. data for transport properties, such as self-diffusivities and viscosities. Dynamical heterogeneity phenomena are quantified through the calculation of the non-Gaussian parameter and the deviation of the self-part of the van Hove correlation function from the expected normal distribution. From this anal., ions that move faster or slower than expected are detected in the system. These subsets of ‘fast’ and ‘slow’ ions form individual clusters consisting of either mobile or immobile ions. Detailed anal. of the ions’ diffusion reveals preferential motion along the direction of the alkyl tail for the cation and along the vector that connects the two sulfur atoms for the anion. For the longest alkyl tails, the heterogeneity in the dynamics becomes more pronounced and is preserved for several nanoseconds, especially at low temperatures In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Category: imidazoles-derivatives).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) 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.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Metal-Controlled Switching of Enantioselectivity in the Mukaiyama-Michael Reaction of α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Chiral Metal-Pybox Complexes was written by Rout, Subhrajit;Das, Arko;Singh, Vinod K.. And the article was included in Journal of Organic Chemistry in 2018.Formula: C6H8N2O This article mentions the following:

Metal-directed switching of enantioselectivity in the Mukaiyama-Michael reaction of silyl enol ethers to α,β-unsaturated 2-acyl imidazoles using the same chiral indapybox ligand I has been reported. The utility of this approach has been portrayed in the synthesis of both enantiomers of optically active δ-keto acid and ester as well as 3,4-dihydropyran-2-one. Moreover, enantioswitching in the construction of the tertiary stereocenter adjacent to a gem-di-Me group has been achieved. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Formula: C6H8N2O).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) 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 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.Formula: C6H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Development of potent small-molecule inhibitors to drug the undruggable steroid receptor coactivator-3 was written by Song, Xianzhou;Chen, Jianwei;Zhao, Mingkun;Zhang, Chengwei;Yu, Yang;Lonard, David M.;Chow, Dar-Chone;Palzkill, Timothy;Xu, Jianming;O’Malley, Bert W.;Wang, Jin. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2016.Product Details of 85692-37-1 This article mentions the following:

Protein-protein interactions (PPIs) play a central role in most biol. processes, and therefore represent an important class of targets for therapeutic development. However, disrupting PPIs using small-mol. inhibitors (SMIs) is challenging and often deemed as “undruggable.”. The authors developed a cell-based functional assay for high-throughput screening to identify SMIs for steroid receptor coactivator-3 (SRC-3 or AIB1), a large and mostly unstructured nuclear protein. Without any SRC-3 structural information, the authors identified SI-2 (I) as a highly promising SMI for SRC-3. SI-2 meets all of the criteria of Lipinski’s rule [Lipinski et al. (2001) Adv Drug Deliv Rev 46(1-3):3-26] for a drug-like mol. and has a half-life of 1 h in a pharmacokinetics study and a reasonable oral availability in mice. As a SRC-3 SMI, SI-2 can selectively reduce the transcriptional activities and the protein concentrations of SRC-3 in cells through direct phys. interactions with SRC-3, and selectively induce breast cancer cell death with IC₅₀ values in the low nanomolar range (3-20 nM), but not affect normal cell viability. Furthermore, SI-2 can significantly inhibit primary tumor growth and reduce SRC-3 protein levels in a breast cancer mouse model. In a toxicol. study, SI-2 caused minimal acute cardiotoxicity based on a hERG channel blocking assay and an unappreciable chronic toxicity to major organs based on histol. analyses. The authors believe that this work could significantly improve breast cancer treatment through the development of “first-in-class” drugs that target oncogenic coactivators. In the experiment, the researchers used many compounds, for example, 1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1Product Details of 85692-37-1).

1-(1-Methyl-1H-imidazol-2-yl)ethanone (cas: 85692-37-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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.Product Details of 85692-37-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cation Alkyl Side Chain Length and Symmetry Effects on the Surface Tension of Ionic Liquids was written by Almeida, Hugo F. D.;Freire, Mara G.;Fernandes, Ana M.;Lopes-da-Silva, Jose A.;Morgado, Pedro;Shimizu, Karina;Filipe, Eduardo J. M.;Canongia Lopes, Jose N.;Santos, Luis M. N. B. F.;Coutinho, Joao A. P.. And the article was included in Langmuir in 2014.SDS of cas: 404001-48-5 This article mentions the following:

The surface tension of two series of ILs, R,R’-dialkylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([C_nC_ni.m.][NTf₂]), and R-alkyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([C_nC₁i.m.][NTf₂]), and their dependence on temperature (from 298 to 343 K) have been studied. For both series of ILs the surface tension decreased with an increase in the cation side alkyl chain length up to aliphatic chains no longer than hexyl, here labeled as critical alkyl chain length (CACL). For ILs with aliphatic moieties longer than CACL the surface tension displayed an almost constant value up to [C₁₂C₁₂i.m.][NTf₂] or [C₁₆C₁i.m.][NTf₂]. These constant values further converged to the surface tension of long chain n-alkanes, indicating that, for sufficiently long alkyl side chains, the surface ordering was strongly dominated by the aliphatic tails present in the IL. The enthalpies and entropies of surface were also derived and the critical temperatures were estimated from the exptl. data. The trend of the derived thermodn. properties highlights the effect of the structural organization of the IL at the surface with visible trend shifts occurring at a well-defined CACL in both sym. and asym. series of ILs. The structure of a long-alkyl side chain IL at the vacuum-liquid interface was explored using mol. dynamics simulations. For the sym. series of ILs, at the outermost polar layers, more cations pointed one of their aliphatic tails outward and the other inward, relative to the surface, than cations pointing both tails outward. The number of the former, while being the preferred conformation, exceeds the latter by around 75%. In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5SDS of cas: 404001-48-5).

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. 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).SDS of cas: 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Evaluation of 1,1-cyclopropylidene as a thioether isostere in the 4-thio-thienopyrimidine (TTP) series of antimalarials was written by Barrows, Robert D.;Hammill, Jared T.;Tran, Michael C.;Falade, Mofolusho O.;Rice, Amy L.;Davis, Christopher W.;Emge, Thomas J.;Rablen, Paul R.;Guy, R. Kiplin;Knapp, Spencer. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Computed Properties of C8H8N2 This article mentions the following:

The 4-(heteroarylthio)thieno[2,3-d]pyrimidine (TTP) series of antimalarials, represented by I and II, potently inhibit proliferation of the 3D7 strain of P. falciparum (EC₅₀ 70-100 nM), but suffer from oxidative metabolism The 1,1-cyclopropylidene isosteres III and IV were designed to obviate this drawback. They were prepared by a short route that featured a combined Peterson methylenation/cyclopropanation transformation of (4-methylthiazol-2-yl)(thieno[2,3-d]pyrimidin-4-yl)methanone. Isosteres III and IV possessed significantly attenuated antimalarial potency. This outcome could be rationalized based on the increased out-of-plane steric demands of the latter two. In support of this hypothesis, the relatively flat (4-methylthiazol-2-yl)(thieno[2,3-d]pyrimidin-4-yl)methanone retained some of the potency of I, even though it appeared to be a comparatively inferior mimic with respect to electronics and bond lengths and angles. Also crystallog. and computationally an apparent increase in the strength of the intramol. sulfur hole interaction of I upon protonation was demonstrated. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Computed Properties of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) 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.Computed Properties of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

C-Acylation of 5-membered N-heterocycles. I. Acylation at C-2 of imidazoles and benzimidazoles was written by Regel, Erik;Buechel, Karl Heinz. And the article was included in Justus Liebigs Annalen der Chemie in 1977.Recommanded Product: 1-Methyl-4-nitroimidazole This article mentions the following:

2-Acylimidazoles (74 compounds) were prepared by acylating imidazoles in the presence of NEt3. 2-Imidazolecarboxylates were similarly obtained with chloroformates. Similar reactions with phthaloyl chlorides gave imidazo[1,2-b]isoquinoline-5,10-diones which underwent ring cleavage to 2-imidazolyl 2-acylphenyl ketones. Benzimidazoles reacted similarly with phthaloyl chlorides. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Recommanded Product: 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) 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-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem