Category: 22468-26-4

Recommanded Product: 4-Hydroxypicolinic acid. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Hydroxypicolinic acid, is researched, Molecular C6H5NO3, CAS is 22468-26-4, about Discovery of novel 3-hydroxypicolinamides as selective inhibitors of HIV-1 integrase-LEDGF/p75 interaction.

Currently, three HIV-1 integrase (IN) active site-directed inhibitors are in clin. use for the treatment of HIV infection. However, emergence of drug resistance mutations have limited the promise of a long-term cure. As an alternative, allosteric inhibition of IN activity has drawn great attention and several of such inhibitors are under early stage clin. development. Specifically, inhibitors of IN and the cellular cofactor LEDGF/p75 remarkably diminish proviral integration in cells and deliver a potent reduction in viral replicative capacity. Distinct from the extensively studied 2-(quinolin-3-yl) acetic acid or 1H-indol-3-yl-2-hydroxy-4-oxobut-2-enoic acid chemotypes, this study discloses a new class of selective IN-LEDGF/p75 inhibitors without the carboxylic acid functionality. More significantly, 3-hydroxypicolinamides also show low micromolar inhibition against IN dimerization, providing novel dual IN inhibitors with in vitro therapeutically selective antiviral effect for further development. Finally, the authors’ shape-based ROCS pharmacophore model of the 3-hydroxypicolinamide class of compounds provides a new insight into the binding mode of these novel IN-LEDGF/p75 inhibitors.

This compound(4-Hydroxypicolinic acid)Recommanded Product: 4-Hydroxypicolinic acid was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Chiral Catalysts,
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Maheshwaran, Athithan; Park, Ho-Yeol; Choi, Jungmin; Sung, Kyungmin; Do, Yeongju; Park, Hyungjin; Kim, Hyein; Song, Myungkwan; Jin, Sung-Ho published an article about the compound: 4-Hydroxypicolinic acid( cas:22468-26-4,SMILESS:O=C(O)C1=NC=CC(O)=C1 ).Product Details of 22468-26-4. 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:22468-26-4) through the article.

Two new highly efficient green emitting heteroleptic Ir(III) complexes, namely, bis[5-(2-ethylhexyl)-8-(trifluoromethyl)benzo[c][1,5]naphthyridin-6(5H)-one]iridium-4-((3,5-di(9H-carbazol-9-yl)benzyl)oxy)picolinate (Ir-HT) and bis[5-(2-ethylhexyl)-8-(trifluoromethyl) benzo[c][1,5]naphthayridin-6(5H)-one]iridium-4-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzyl) oxy)picolinate (Ir-ET) were designed and synthesized for solution-processed phosphorescence organic light-emitting diodes (PHOLEDs). These new Ir(III) complexes are based on amide-bridged trifluoromethyl (-CF3) substituted phenylpyridine unit as main ligand and 1,3-bis(N-carbazolyl)benzene (mCP) unit and 1,3,4-oxadiazole (OXD) unit functionalized picolinate (pic) as an ancillary ligand. These multifunctional groups were attached into the 4-position of pic ancillary ligands via ether linkage. Interestingly, the solution-processed PHOLED device using Ir-HT as a dopant exhibited a maximum external quantum efficiency (EQEmax) of 20.92% and a maximum current efficiency (CEmax) of 64.04 cd A-1. Whereas PHOLED device using Ir-ET displayed a EQEmax of 20.68% and a CEmax of 65.02 cd A-1. This is one of best CE with high EQE for green Ir(III) complexes via solution-processed PHOLEDs using multifunctional ancillary ligands so far.

《Green Ir(III) complexes with multifunctional ancillary ligands for highly efficient solution-processed phosphorescence organic light-emitting diodes with high current efficiency》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(4-Hydroxypicolinic acid)Product Details of 22468-26-4.

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Chiral Catalysts,
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Recommanded Product: 4-Hydroxypicolinic acid. 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: 4-Hydroxypicolinic acid, is researched, Molecular C6H5NO3, CAS is 22468-26-4, about Design, synthesis and biological evaluation of second-generation benzoylpiperidine derivatives as reversible monoacylglycerol lipase (MAGL) inhibitors. Author is Granchi, Carlotta; Bononi, Giulia; Ferrisi, Rebecca; Gori, Eleonora; Mantini, Giulia; Glasmacher, Sandra; Poli, Giulio; Palazzolo, Stefano; Caligiuri, Isabella; Rizzolio, Flavio; Canzonieri, Vincenzo; Perin, Tiziana; Gertsch, Jurg; Sodi, Andrea; Giovannetti, Elisa; Macchia, Marco; Minutolo, Filippo; Tuccinardi, Tiziano; Chicca, Andrea.

An interesting enzyme of the endocannabinoid system is monoacylglycerol lipase (MAGL). This enzyme, which metabolizes the endocannabinoid 2-arachidonoylglycerol (2-AG), has attracted great interest due to its involvement in several physiol. and pathol. processes, such as cancer progression. Exptl. evidences highlighted some drawbacks associated with the use of irreversible MAGL inhibitors in vivo, therefore the research field concerning reversible inhibitors is rapidly growing. In the present manuscript, the class of benzoylpiperidine-based MAGL inhibitors was further expanded and optimized. Enzymic assays identified some compounds in the low nanomolar range and steered mol. dynamics simulations predicted the dissociation itinerary of one of the best compounds from the enzyme, confirming the observed structure-activity relationship. Biol. evaluation, including assays in intact U937 cells and competitive activity-based protein profiling experiments in mouse brain membranes, confirmed the selectivity of the selected compounds for MAGL vs. other components of the endocannabinoid system. Future studies on the potential use of these compounds in the clin. setting are also supported by the inhibition of cell growth observed both in cancer organoids derived from high grade serous ovarian cancer patients and in pancreatic ductal adenocarcinoma primary cells, which showed genetic and histol. features very similar to the primary tumors.

《Design, synthesis and biological evaluation of second-generation benzoylpiperidine derivatives as reversible monoacylglycerol lipase (MAGL) inhibitors》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(4-Hydroxypicolinic acid)Recommanded Product: 4-Hydroxypicolinic acid.

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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 X-ray contrast agents. II. Synthesis of iodine compounds of α-picoline, published in 1954, which mentions a compound: 22468-26-4, mainly applied to , Quality Control of 4-Hydroxypicolinic acid.

Two new x-ray contrast agents, 3,5-diiodo-4-hydroxy-α-picoline (I) and 2-methyl-3,5-diiodo-4-pyridone-1-acetic acid (II) were prepared from α-picoline. 4-Chloro-α-picoline (2.6 g.), 3 g. AcONa, and 15 ml. AcOH heated 8 hrs. at 200°, the solvent evaporated in vacuo, the residue heated 1 hr. with 10% HCl, the mixture evaporated to dryness, taken up in EtOH, mixed with 5 ml. saturated aqueous NaHCO3, again evaporated, and dissolved in benzene gave 1.7 g. 4-hydroxy-α-picoline (III), m.p. indefinite; picrate, m. 199-200° (from MeOH). III (0.5 g.) dissolved in 20 ml. hot H2O containing 3 ml. concentrated HCl, treated with 1.8 g. ClI in 10% HCl, heated 0.5 hr. on water bath, the mixture diluted with 100 ml. hot H2O, acid added, the mixture cooled, the precipitate dissolved in NaOH solution and precipitated with dilute HCl gave 1.6 g. I, decomposing 239-41°. I (1 g.) in 10 ml. 10% NaOH refluxed 3 hrs. with 0.3 g. CH2ClCO2H in 4 ml. 10% Na2CO3, cooled, filtered, and the filtrate neutralized with 10% HCl gave 1 g. II, decomposing 230-2° (from dilute pyridine). III (1.5 g.) in 5 ml. 10% NaOH treated portionwise with 4.4 g. KMnO4 in 200 ml. of H2O at 80° with stirring, stirring and heating continued, the MnO2 filtered off, the filtrate neutralized with HCl and AcOH, evaporated, and cooled gave 4-pyridone-2-carboxylic acid (IV), decomposing 249-57° (from EtOH-benzene). 3,5-Diiodo-4-pyridone-2-carboxylic acid, decomposing 250-5°, was prepared from IV by the procedure of Dohrn and Diedrich (C.A. 26, 3506) and in a smaller yield by oxidizing I with KMnO4. 2,5-Diiodo-2-carboxy-4-pyridone-1-acetic acid, decomposing 223-4°, and 3,5-diiodo-1-methyl-4-pyridone-2-carboxylic acid, m. 159°, were prepared from the appropriate intermediates by the method of D. and D. (loc. cit.).

Different reactions of this compound(4-Hydroxypicolinic acid)Quality Control of 4-Hydroxypicolinic acid require different conditions, so the reaction conditions are very important.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 22468-26-4, is researched, SMILESS is O=C(O)C1=NC=CC(O)=C1, Molecular C6H5NO3Journal, Comparative Study, Article, Research Support, U.S. Gov’t, P.H.S., Brain Research called Structure-function relationships for kynurenic acid analogs at excitatory pathways in the rat hippocampal slice, Author is Robinson, Michael B.; Schulte, Marvin K.; Freund, Ronald K.; Johnson, Rodney L.; Koerner, James F., the main research direction is kynurenate structure function hippocampus.COA of Formula: C6H5NO3.

Eight kynurenic acid analogs were bath-applied to rat hippocampal slices while recording extracellular synaptic field potentials, and the potencies of these analogs for inhibition of these responses were compared to that of kynurenic acid  [492-27-3]. Quinaldic acid  [93-10-7], 4-hydroxyquinoline  [611-36-9], 4-hydroxypicolinic acid  [22468-26-4], L-kynurenine  [2922-83-0], and picolinic acid  [98-98-6] inhibited evoked field potentials, but were at least 15-fold less potent than kynurenic acid in all pathways tested. Xanthurenic acid  [59-00-7] was inactive in the pathways tested. Quinolinic acid  [89-00-9] and dipicolinic acid  [499-83-2] showed signs of agonist activity with half-max ID’s of approx. 400 μM and 2500 μM, resp. Evidently, the 2-carboxy group and the 4-hydroxy moiety are essential for the antagonist activity exhibited by kynurenate. The unsubstituted 2nd aromatic ring greatly enhances the affinity of kynurenate for these receptors, and substitution in at least 1 position on this aromatic ring abolishes activity.

Different reactions of this compound(4-Hydroxypicolinic acid)COA of Formula: C6H5NO3 require different conditions, so the reaction conditions are very important.

Reference:
Chiral Catalysts,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Action of thionyl chloride on the pyridinemonocarboxylic acids》. Authors are Meyer, Hans; Graf, Roderich.The article about the compound:4-Hydroxypicolinic acidcas:22468-26-4,SMILESS:O=C(O)C1=NC=CC(O)=C1).Application of 22468-26-4. Through the article, more information about this compound (cas:22468-26-4) is conveyed.

M. and others had obtained by the action of SOCl2 on pyridinecarboxylic acids substances having the properties of acid chlorides but which, because of their abnormally high m. ps. were thought to be polymers, while Späth and Spitzer (C, A. 20, 3294) later obtained products with normally low m. ps. A renewed study of the reaction has now revealed the cause of the discrepancy. If the treatment of picolinic acid (I) with SOCl2 is not too prolonged there is obtained almost exclusively the normal low-melting chloride (II) but if it is continued longer nucleus chlorination also takes place, especially at high temperatures Nicotinic (III) and isonicotinie acids (IV) are not appreciably halogenated in the nucleus at the b. p. of SOCl2 but do yield chlorinated derivatives when heated in sealed tubes. If the crude II, still containing SOCl2, is kept in vacuo over KOH the originally liquid mass gradually changes into the high-melting product previously thought to be the polymer but which is really II. HCl and finally changes into I.HCl. This change into II.HCl occurs only in the presence of traces of H2O. The conversion of II.HCl into I.HCl is at first very rapid but gradually becomes slower and slower so that the resulting mixture shows for many hrs. an almost constant Cl content, the presence of I.HCl being thereby masked. As in the earlier experiments fresh products were used for the preparation of the amide and esters while the analyses were made only after they no longer gave off penetrating vapors it is easy to understand why the error as to their true nature was made. The admixed SOCl2 can readily be removed completely in vacuo but the now completely S-free products still evolve for a long time penetrating vapors which, however, do not originate in an excess of SOCl2 still present but represent the HCl set free in the change of II.HCl into I.HCl. III and IV behave in the same way but the change of the chloride HCl salts into the acid HCl salts is materially slower. Sublimed II, prepared according to Späth and Spitzer, m. 46°, gives 80% of the amide with NH3, is stable in C6H6 even in the light or in scaled tubes at 100° but in the crystalline form changes in a few hrs. into a green-black mass even if protected from light and air. II.HCl, readily obtained from II in C6H6 with HCl, is a powdery precipitate which, when heated under the supernatant fluid in a scaled vessel until dissolved and allowed to cool slowly, seps. in leaflets, whereas on heating in an open dish it loses HCl and changes into I.HCl; it is extraordinarily hygroscopic and rapidly decomposes in the air into I.HCl and HCl, but when protected from the air it can be kept for months without appreciable change; in a scaled capillary it m. 118-22° (decomposition). Chloride of III, best prepared by refluxing its HCl salt 3 days in SOCl2, b12 85°, m. 15-6°. Chloride of IV, b. 100° in the vacuum of a H2O pump, m, 15-6°. 4-Chloropicolinic acid (V) (30-40% from 10 g. I.HCl boiled in 30 cc. SOCl2 until dissolved, and then heated 20 hrs. at 100°, the resulting HCl salt being decomposed with boiling H2O) m. 182° (decomposition); its NH4 salt with concentrated NH4OH at 180° gives aminopicolinic acid, m. 260° (decomposition) (isolated through the light violet Cu salt), which above its m. p. loses CO2 and yields quant. 4-C5H4NNH2, m. 157-8°, while on diazotization it yields 4-hydroxypicolinic acid, m. 254-5° with evolution of CO2 and formation of 4-C5H4NOH, m. 65-6°. Chloride of V, m. 46°, can be distilled in vacuo without decomposition Me ester, m. 57-8°. Ph ester, m. 68°. Amide, m. 158°. 4,6-Dichloropicolinic acid (VI) (35% from 5 g. V and 15 cc. SOCl2 heated 50 hrs. at 180°), needles (from dilute solution) or leaflets (from concentrated solution) with 1H2O, m. 96-7°, sublimes in anhydrous spears, m. 111-2°, loses HCl at 160-70° and changes into a solid which melts very much higher with decomposition V refluxed in HI (b. 127°) with red P gives a basic 4-iodopicolinic acid-HI (VII), C12H9O4N2I3, m. 185-90°, converted in hot H2O by an excess of freshly precipitated AgCl into the free acid (18 g. from 12 g. V), m. 169° (decomposition); Me ester, m. 75-6°. VI boiled with HI (d. 1.7) and red P gives VII. Me ester of VI, m. 73-4°. Amide, m. 172-4°. 3(5),4,6,-Trichloropicolinic acid is obtained as a by-product in the preparation of VI; its Me ester m. 122-3°. 5-Chloronicotinic acid, m. 171° is obtained in very small yield from III.HCl with SOCl2 at 180°, followed by saponification with boiling H2O; chloride, b12 120°, m. 53°; Me ester, m. 88-9°; Ph ester, m. 79°; amide, m. 205-6°. The NH4 salt with NH4 salt with NH4OH and CuO at 180° yields 5-aminonicotinicotinic acid (Me ester, m. 137°) which above its m. p. forms 3-C6H4NNH2. 5,6-Dichloronicotinic acid (30% from III.HCl heated 50 hrs. with SOCl2 at 150°), needles with 1H2O, m. (anhydrous) 161-2°, resolidifies a few degrees higher and m. again about 300° (decomposition); boiled a long time in excess of KOH or with moderately concentrated H2SO4 it gives the 5-chloro-6-hydroxy acid, m. 305° (incipient decomposition). From. IV and SOCl2 at 180-220° are obtained 3-chloroisonicotinic acid (VII), m. 235° (sealed capillary) (Me ester, m. 32°), and 3,5-dichloroisonicotinic acid (VIII), m. 218.20°, sublimes without decomposition in vacuo. 3-Hydroxyisonicotinic acid, from VII in boiling 50% KOH, yellowish, m. 312°. VIII heated 20 hrs. at 230° yields 3,5-dichloropyridine (IX), m. 64-5°, has an intense odor and is extraordinarily volatile; it was also synthesized from 5-chloronicotinic acid through the Me ester, hydrazide (m. 178°), urethan and 3,5-C5H3N(NH2)Cl. 2,5-Dichloropyridine, from Me isocinchomeronate through 2,5-C5H3N(NH2)2 treated in concentrated HCl with NaNO2 and Cu2Cl2, extremely volatile, m. 60°, depresses the m. p. of IX more than 20°.

The article 《Action of thionyl chloride on the pyridinemonocarboxylic acids》 also mentions many details about this compound(22468-26-4)Application of 22468-26-4, you can pay attention to it, because details determine success or failure

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-Hydroxypicolinic acid(SMILESS: O=C(O)C1=NC=CC(O)=C1,cas:22468-26-4) is researched.Synthetic Route of C6H5NO3. The article 《Optimization of an azetidine series as inhibitors of colony stimulating factor-1 receptor (CSF-1R) Type II to lead to the clinical candidate JTE-952》 in relation to this compound, is published in Bioorganic & Medicinal Chemistry Letters. Let’s take a look at the latest research on this compound (cas:22468-26-4).

Optimization of novel azetidine compounds, which we had found as colony stimulating factor-1 receptor (CSF-1R) Type II inhibitors, provided JTE-952 as a clin. candidate with high cellular activity (IC50 = 20 nM) and good pharmacokinetics profile. JTE-952 was also effective against a mouse collagen-induced model of arthritis (mouse CIA-model). Addnl., the x-ray co-crystal structure of JTE-952 with CSF-1R protein was shown to be a Type II inhibitor, and the kinase panel assay indicated that JTE-952 had high kinase selectivity.

The article 《Optimization of an azetidine series as inhibitors of colony stimulating factor-1 receptor (CSF-1R) Type II to lead to the clinical candidate JTE-952》 also mentions many details about this compound(22468-26-4)Category: chiral-catalyst, you can pay attention to it, because details determine success or failure

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Menendez Rodriguez, Gabriel; Bucci, Alberto; Hutchinson, Rachel; Bellachioma, Gianfranco; Zuccaccia, Cristiano; Giovagnoli, Stefano; Idriss, Hicham; Macchioni, Alceo researched the compound: 4-Hydroxypicolinic acid( cas:22468-26-4 ).Synthetic Route of C6H5NO3.They published the article 《Extremely Active, Tunable, and pH-Responsive Iridium Water Oxidation Catalysts》 about this compound( cas:22468-26-4 ) in ACS Energy Letters. Keywords: hydroxy pyridine carboxylate iridium water oxidation catalyst synthesis. We’ll tell you more about this compound (cas:22468-26-4).

The development of an efficient water oxidation catalyst is crucial in the framework of constructing an artificial photo(electro)synthetic apparatus for the production of solar fuels. Herein, new hydroxy-pyridine-carboxylate iridium complexes are reported exhibiting high activity in water oxidation with both cerium ammonium nitrate and NaIO4 as sacrificial oxidants. With the latter, the catalytic activity strongly depends on the pH and position of the OH-substituent in the pyridine ring, reaching a record turnover frequency of 458 min-1 and turnover number ( > 14500) limited only by the amount of NaIO4. Kinetic experiments measuring O2 evolution paralleled by NMR studies on oxidative transformation with NaIO4 suggest that Cp* of the catalyst is readily degraded, whereas the hydroxy-pyridine-carboxylate ligands remain coordinated at iridium, tuning its activity.

The article 《Extremely Active, Tunable, and pH-Responsive Iridium Water Oxidation Catalysts》 also mentions many details about this compound(22468-26-4)Synthetic Route of C6H5NO3, you can pay attention to it, because details determine success or failure

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Chiral Catalysts,
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Computed Properties of C6H5NO3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Hydroxypicolinic acid, is researched, Molecular C6H5NO3, CAS is 22468-26-4, about Synthesis and biological evaluation of a series of novel pyridinecarboxamides as potential multi-receptor antipsychotic drugs. Author is Xu, Mingshuo; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen; Ye, Bin; Jiang, Xiangrui; Zhao, Qingjie; Li, Jianfeng; Liu, Yongjian; Zhang, Junchi; Tian, Guanghui; He, Yang; Shen, Jingshan; Jiang, Hualiang.

In previous study, a series of benzamides was identified as potent antipsychotic agents. As a continuation of the program to discover antipsychotics, herein we reported the evaluation of a series of pyridinecarboxamide derivatives The most promising compound I not only held good activities on dopamine D2, serotonin 5-HT1A and 5-HT2A receptors, but also exhibited low potency for α1A, H1 and 5-HT2C receptors, indicating a low propensity of side effects like orthostatic hypotension and weight gain. Furthermore, I exhibited more potent antipsychotic-like effect than aripiprazole in behavioral studies. The preliminary results were promising enough for further research around this scaffold.

After consulting a lot of data, we found that this compound(22468-26-4)Computed Properties of C6H5NO3 can be used in many types of reactions. And in most cases, this compound has more advantages.

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Yasarawan, Nuttawisit; Thipyapong, Khajadpai; Ruangpornvisuti, Vithaya published an article about the compound: 4-Hydroxypicolinic acid( cas:22468-26-4,SMILESS:O=C(O)C1=NC=CC(O)=C1 ).Computed Properties of C6H5NO3. 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:22468-26-4) through the article.

Comparative study on kinetics and thermodn. of proton-related reactions of hydroxypicolinic acids was carried out using d. functional theory associated with polarizable continuum model of solvation. Mechanisms for such reactions were established. Both 3- and 4-hydroxypicolinic acid prefer zwitterionic forms to normal forms. For 6-hydroxypicolinic acid, keto forms are highly preferred. The pKa values and UV/visible bands predicted for some picolinic compounds agree with the experiment 5-Hydroxypicolinate shows the highest preference for complexation with copper(II) but 6-hydroxypolinate gives rise to the most stable complex. Kinetic stability of the trans-isomer relative to the cis-isomer of the complexes was evaluated. UV/visible spectral data predicted for some picolinate complexes are also in agreement with the previous experiment

Although many compounds look similar to this compound(22468-26-4)Computed Properties of C6H5NO3, numerous studies have shown that this compound(SMILES:O=C(O)C1=NC=CC(O)=C1), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

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Chiral Catalysts,
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