Tag: M.W:200-300

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Nature Chemistry called Concerted nucleophilic aromatic substitutions, Author is Kwan, Eugene E.; Zeng, Yuwen; Besser, Harrison A.; Jacobsen, Eric N., which mentions a compound: 26218-78-0, SMILESS is C1=NC(=CC=C1C(=O)OC)Br, Molecular C7H6BrNO2, Electric Literature of C7H6BrNO2.

Nucleophilic aromatic substitution (SNAr) is one of the most widely applied reaction classes in pharmaceutical and chem. research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for SNAr reactions involves a two-step addition-elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here the authors use 12C/13C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical SNAr reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of 19F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C-F bonds.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called In vitro DNA synthesis. DNA activation necessary for the reaction by liver-homogenate supernatants in compensatory hypertrophy and hepatoma. Implicated enzymic mechanisms, published in 1964, which mentions a compound: 3066-84-0, mainly applied to , Reference of 8-Bromoguanine.

cf. CA 62, 3181g. The progressive transformation of native DNA into primer DNA in the presence of rat liver homogenate supernatants previously reported has been shown not to be due to action of the DNases I and II of these supernatants, but should probably be attributed to an enzyme of the type DNA-phosphatase-exonuclease, described by Richardson, et al. (CA 60, 5810f).

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Tetrahydrofuran – Wikipedia,
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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 8-Bromoguanine( cas:3066-84-0 ) is researched.Computed Properties of C5H4BrN5O.Abdou, Ibrahim M.; Boone, Edna K.; Cao, Huachuan; Crummie, Cheryl; Schuster, Gary B. published the article 《Transport and reactions of radical cations in DNA: Steric and energetic control of reactivity》 about this compound( cas:3066-84-0 ) in Research on Chemical Intermediates. Keywords: radical cation transport reaction DNA. Let’s learn more about this compound (cas:3066-84-0).

A series of DNA oligomers was prepared that contain an anthraquinone group (AQ) linked to a 5′-terminus and have 8-methylguanine (MG) or 8-bromoguanine (BG) substituted for G at various positions. Irradiation of the AQ injects a radical cation into the oligonucleotide, which migrates through the DNA and reacts primarily at Gn sites where n = 2 or 3. Substitution with MG, which has an oxidation potential (EOX) slightly below G, traps the migrating radical cation, substitution with BG, which has an EOX above G, does not. However, both MG and BG affect the relative reactivity of the guanines in Gn steps. Moreover, a (G)3 sequence has a much smaller effect on the efficiency of radical cation migration than does MG, which demonstrates that the EOX of G in the (G)3 sequence is above that of MG. These findings show that the EOX of the base controls the efficiency of radical cation transport and that steric effects influence the relative reactivity of G in Gn sequences.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Electric Literature of C7H6BrNO2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Probing the metabotropic glutamate receptor 5 (mGlu5) positive allosteric modulator (PAM) binding pocket: discovery of point mutations that engender a “”molecular switch”” in PAM pharmacology. Author is Gregory, Karen J.; Nguyen, Elizabeth D.; Reiff, Sean D.; Squire, Emma F.; Stauffer, Shaun R.; Lindsley, Craig W.; Meiler, Jens; Conn, P. Jeffrey.

Pos. allosteric modulation of metabotropic glutamate receptor subtype 5 (mGlu5) is a promising novel approach for the treatment of schizophrenia and cognitive disorders. Allosteric binding sites are topog. distinct from the endogenous ligand (orthosteric) binding site, allowing for co-occupation of a single receptor with the endogenous ligand and an allosteric modulator. Neg. allosteric modulators (NAMs) inhibit and pos. allosteric modulators (PAMs) enhance the affinity and/or efficacy of the orthosteric agonist. The mol. determinants that govern mGlu5 modulator affinity vs. cooperativity are not well understood. Focusing on the modulators based on the acetylene scaffold, the authors sought to determine the mol. interactions that contribute to PAM vs. NAM pharmacol. Generation of a comparative model of the transmembrane-spanning region of mGlu5 served as a tool to predict and interpret the impact of mutations in this region. Application of an operational model of allosterism allowed for determination of PAM and NAM affinity estimates at receptor constructs that possessed no detectable radioligand binding as well as delineation of effects on affinity vs. cooperativity. Novel mutations within the transmembrane domain (TM) regions were identified that had differential effects on acetylene PAMs vs. 2-methyl-6-(phenylethynyl)-pyridine, a prototypical NAM. Three conserved amino acids (Y658, T780, and S808) and two non-conserved residues (P654 and A809) were identified as key determinants of PAM activity. Interestingly, the authors identified two point mutations in TMs 6 and 7 that, when mutated, engender a mode switch in the pharmacol. of certain PAMs.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Recommanded Product: 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione, is researched, Molecular C13H20N4O2, CAS is 1028-33-7, about Non-human primate SPECT model for determining cerebral perfusion effects of cerebrovasoactive drugs acting via multiple modes of pharmacological action. Author is Oliver, Douglas W.; Dormehl, Irene C.; Louw, Werner K. A..

Increasing clin. and exptl. evidence implicate cerebral hypoperfusion during increased aging and points to chronic cerebrovascular ischemia as a vital component of the neuropathol. progression of dementia. In vivo cerebral perfusion animal models can greatly contribute to the evaluation of drugs and to the screening of drug interactions. This study describes a baboon Papio ursinus model under anesthesia, for in vivo cerebral blood flow (CBF) determinations, using Single Photon Emission Computed Tomog. (SPECT) following the split-dose method with 99mTc-hexamethylpropylene amine oxime (99mTc-HMPAO). Perfusion studies with acetazolamide as intervention clearly showed that the non-human primate model under aneasthesia is sufficiently sensitive to serve in the evaluation of other cerebrovasoactive drugs for induced perfusion changes with significant increases of the R-value (+40%) for comparative measurement when compared to the control value (2.53±0.15 vs. 1.79±0.13). These findings stimulated investigations of several drugs, i.e. pentifylline (phosphodiesterase inhibitor); nimodipine (calcium channel blocker); sumatriptan (serotonin receptor agonist) and nicotinic acid (vasodilator) for CBF effects. Increases in the cerebral perfusion in some cases more than +30% for nimodipine (2.51±0.14 vs. 1.79±0.13), acetazolamide and +29% for the combination of pentifylline and nicotinic acid (2.31±0.19 vs. 1.79±0.13) were observed Drug interaction studies revealed an attenuation of increased CBF due to nimodipine, with sumatriptan (-25%) and acetazolamide (+22%) in combination with nimodipine. Drug interactions with clin. implications may result during simultaneous use of cerebrovasoactive drugs in managing patients with cerebrovascular disorders. This study further showed that the CBF non-human primate model under anesthesia is useful for the investigation of vasoactive drugs acting via various pharmacol. modes of action.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Goodman, Michael G.; Weigle, William O. published an article about the compound: 8-Bromoguanine( cas:3066-84-0,SMILESS:NC(N1)=NC(NC(Br)=N2)=C2C1=O ).Quality Control of 8-Bromoguanine. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:3066-84-0) through the article.

8-Bromoguanosine (88rGuo), a low mol.weight nucleoside derivative that rapidly traverses the lymphocyte membrane to the interior of the cell, is an extremely potent inducer of Ig production by B lymphocytes. 88Br-cGMP and other cGMP analogs are at best weak inducers of Ig secretion, being >2 orders of magnitude less effective (per mol. taken up) then 8BrGuo. Incubation of lymphocytes with 88rGuo fails to elevate their intracellular concentrations of cGMP. Moreover, at equimolar concentrations, underivatized cGMP actually antagonizes the induction of antibody production by 8BrGuo. These data, in concert with observations that many lymphocyte activators fail to alter cGMP content, that many agents that elevate cGMP fail to induce Ig synthesis, and that some cGMP-elevating agents even inhibit it, suggest that the induction of proliferation in B cells, is not primarily dependent upon cGMP. A simple nucleoside derivative is described, the use of which should prove to be a powerful probe for investigating the triggering mechanisms underlying the proliferative and differentiative B lymphocyte pathways at the mol. level.

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Tetrahydrofuran – Wikipedia,
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Safety of 8-Bromoguanine. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 8-Bromoguanine, is researched, Molecular C5H4BrN5O, CAS is 3066-84-0, about Functional groups on ‘Z’ DNA recognized by monoclonal antibodies. Author is Lee, Jeremy S.; Woodsworth, Mary L.; Latimer, Laura J. P..

Both brominated poly[d(GC)] and poly[d(Gm5C), where m5C = 5-methylcytidylate] form stable left-handed Z-DNA structures at physiol. ionic strengths. These 2 antigens were used to prepare monoclonal antibodies from immunized mice. The specificity of the antibodies was studied in detail with a solid-phase radioimmune assay as well as by competition experiments Both immunogens produced several relatively nonspecific antibodies, but 2 types of very specific antibody were also distinguished. The 1st binds poly[d(Gm5C)] but not brominated poly[d(GC)], whereas the other has the opposite specificity and will only bind the brominated polymer. In these studies, monoclonal antibodies are used as model proteins for Z DNA functional group recognition.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Mishra, S. K.; Mishra, P. C. published the article 《An ab initio study of electronic structure and spectra of 8-bromoguanine: a comparative study with guanine》. Keywords: bromoguanine tautomer ab initio electronic structure fluorescence; MP2 RHF electronic structure bromoguanine; isodensity surface polarized continuum electronic structure bromoguanine.They researched the compound: 8-Bromoguanine( cas:3066-84-0 ).Formula: C5H4BrN5O. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:3066-84-0) here.

Ground state geometries of the four tautomeric forms keto-N9H, keto-N7H, enol-N9H and enol-N7H of 8-bromoguanine (8BG) were optimized using the ab initio RHF procedure employing a mixed basis set consisting of the 6-311+G* basis set for the nitrogen atom of the amino group and the bromine atom, and the 4-31G basis set for all other atoms. These calculations were followed by correlation correction of the total energy at the MP2 level using the same basis set. The different tautomeric forms of 8BG in the ground state were solvated using the isodensity surface polarized continuum model (IPCM) of the SCRF theory both at the RHF and MP2 levels. Excited states were generated employing CI among singly excited configurations (CIS) obtained using a limited window of filled and empty MOs. Formation of hydrogen-bonded complexes between 8BG and three water mols. in the ground and excited states was considered in order to account for solvent effects approx. Excited state geometry was optimized in each case for the lowest singlet excited state which was found to be of π-π* type. Vibrational frequency anal. was performed in order to ensure that the stationary points located on the potential energy surfaces by geometry optimization were min. It is found that 8BG would occur in the ground state dominantly in the keto-N7H form both at the aqueous solution-air interface and inside the bulk liquid The observed absorption and fluorescence spectra of 8BG can be explained satisfactorily considering only the keto-N7H form of the mol. The enol tautomers of 8BG do not appear to be important from the point of view of ground state properties or electronic spectra. The observed differences between the behaviors of guanine and 8BG can be easily explained on the basis of the results obtained.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Electric Literature of C14H24O4. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-(((1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl)oxy)-4-oxobutanoic acid, is researched, Molecular C14H24O4, CAS is 77341-67-4, about Synthesis and properties of new (-)-menthol-derived chiral liquid crystal compounds with alkyl or alkoxy terminal groups. Author is Jia, Ying-Gang; Luo, Cong-Cong; Zhu, Zhao-Xia; Hu, Jian-She.

Two series of chiral mesogenic compounds derived from (-)-menthol with varying length of alkyl or alkoxy terminal groups resp. were designed and synthesized. Their chem. structures were characterized by FT-IR and 1H-NMR spectra. The thermal properties and optical textures were investigated by differential scanning calorimetry and polarizing optical microscopy. Bragg selective reflection spectra of the compounds with the alkoxy chain in the N* phase were measured by UV/visible spectrometer. The results showed that the alkyl series homologues melt directly to the isotropic phase on heating and display cubic blue phase and focal conic textures of chiral nematic phase on cooling, whereas the alkoxy series displayed oily streak textures with iridescent colors on heating, and platelet textures of blue phase and focal conic textures were observed on cooling cycles. The chain structure and length of the terminal groups have profound influence on the isotropic temperature and a large odd-even effect is observed for the compounds The selective reflection colors of alkoxy series shifted to longer wavelength with the increasing of temperature

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Tetrahydrofuran – Wikipedia,
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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Using Density Functional Theory To Design DNA Base Analogues with Low Oxidation Potentials, published in 2001-07-12, which mentions a compound: 3066-84-0, Name is 8-Bromoguanine, Molecular C5H4BrN5O, COA of Formula: C5H4BrN5O.

The oxidizability of substituted nucleobases was evaluated through theor. calculations and the ability of individual bases to induce current enhancement in the cyclic voltammograms of metal complexes. Formation of the guanine derivatives 7-deazaguanine and 8-oxoguanine is known to lower the energy for oxidation of guanine. The similar derivatives of adenine were examined and gave lower predicted redox energies as well as current enhancement with Ru(bpy)32+ (7-deazaadenine) and Fe(bpy)32+ (8-oxoadenine). Oxidizable, substituted pyrimidines were identified using a computational library that gave 5-aminocytosine and 5-aminouracil as promising electron donors. Again, these predictions were verified using catalytic electrochem. In addition, the computations predicted that 6-aminocytosine would be redox-active but not as easily oxidized as 5-aminocytosine, which was also confirmed exptl. In addition to calculating the relative one-electron redox potentials, we used calculations to evaluate the loss of a proton that occurs from the initially formed radical cation. These calculations gave results consistent with the experiments, and in the case of 8-oxoadenine, the relative redox reactivity could be predicted only when the proton loss step was considered. These substituted bases constitute building blocks for highly redox-active nucleic acids, and the associated theor. model provides powerful predictability for designing new redox-active nucleobases.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem