Day: April 6, 2022

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 Preparation and acetylcholinesterase inhibitory activities of pyridine-based 1,3,4-oxadiazole derivatives, published in 2020, which mentions a compound: 3326-71-4, mainly applied to pyridinyl oxadiazole preparation acetylcholinesterase inhibition SAR docking, Recommanded Product: 3326-71-4.

Fourteen pyridine-based 1,3,4-oxadiazole derivatives I [R = n-Bu, Ph, 3-pyridyl, etc.] were synthesized from pyridine-2-carboxaldehyde via iodine-mediated oxidative cyclization with substituted hydrazides by using the impregnation method. Their structures were confirmed by m.p., 1H NMR, 13C NMR and HRMS. Preliminary bioassay of these derivatives I, inhibition of acetylcholinesterase (AChE) was also evaluated in-vitro at the concentration of 1μmol/mL. The result showed that compounds I [R = 3-methoxyphenyl, 3-pyridyl, 4-pyridyl] had moderate inhibitory activities with 52%, 59% and 59%, resp. The preliminary structure-activity relationships revealed that the introduction of pyridine ring could enhance the activity. Mol. docking study demonstrated that compound I [R = 4-pyridyl] possessed an optimal docking pose with interactions at the middle of the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Related Products of 610-09-3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about FT-IR and FT-Raman spectroscopy study of the cyclic anhydride intermediates for the esterification of cellulose. Part 3. Cyclic anhydrides formed by the isomers of cyclohexanedicarboxylic acid. Author is Yang, Charles Q.; Zhang, Guobao.

Multifunctional carboxylic acids were used as crosslinking agents for cotton and wood pulp cellulose. In the authors’ previous research, the authors found that a polycarboxylic acid esterifies cellulose through the formation of a 5-membered cyclic anhydride intermediate by the dehydration of 2 carboxyl groups. The authors studied the formation of those cyclic anhydride intermediates by different isomers of cyclohexanedicarboxylic acid (CHA) so that the authors can elucidate the effects of mol. structure on the formation of the anhydride intermediates. The authors found that both cis- and trans-1,2-CHA form 5-membered anhydride intermediates when temperature reaches their m.p. and that cis-1,2-CHA forms the cyclic anhydride at temperatures lower than does trans-1,2-CHA. 1,3-CHA forms 6-membered cyclic anhydride at temperatures much higher than its m.p. The formation of a 5-membered cyclic anhydride intermediates takes place at temperatures lower than that of a 6-membered anhydride. This is probably the main reason why those polycarboxylic acids with their carboxylic acid groups bonded to the adjacent carbons of the mol. backbones are more effective crosslinking agents for cellulose than those with their carboxylic groups bonded to the alternative carbons. No formation of cyclic anhydride was found for 1,4-CHA. The formation of a 5-membered cyclic anhydride was accelerated by monosodium phosphate, which is used as a catalyst for the esterification of cotton cellulose by polycarboxylic acids.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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 Design and synthesis of new pyranoquinolinone heteroannulated to triazolopyrimidine of potential apoptotic antiproliferative activity, published in 2020-12-31, which mentions a compound: 3326-71-4, mainly applied to pyranoquinolinone triazolopyrimidine apoptosis antiproliferative formimidic acid; Antiproliferative; Apoptosis; Caspase; Formimidic acid; Pyrano[3,2-c]quinoline; Triazolopyrimidine, Quality Control of 2-Furoic hydrazide.

Pyrano[3,2-c]quinoline derivatives have been synthesized and utilized to obtain various new hetero-annulated triazolopyrimidine, containing quinoline, pyran, 1,2,4-triazine and pyrimidine in good yields. Newly synthesized compounds have been characterized by spectral data and elemental anal. Most of the synthesized compounds showed moderate to weak antiproliferative activity on most cancer cell lines, especially leukemia and breast cancer cell lines. The open chain formimidic acid Et ester is slightly more potent than hetero-annulated systems. The most active compounds were further investigated for caspase activation, Bax activation and Bcl-2 down regulation compared to doxorubicin as a standard, and indeed exhibited mainly cell cycle arrest at the Pre-G1 and G2/M phases. The transcription effects of 5a and 5b on the p53 were assessed and compared with the reference doxorubicin. The results revealed an increase of 12-19 in p53 level compared to the test cells and that p53 protein level of 5a and 5b was significantly inductive (991, and 639 pg/mL, resp.) in relation to doxorubicin (1263 pg/mL).

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Application of 610-09-3. 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: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about [Ni(cyclam)]2+ and [Ni(R,S-Me6cyclam)]2+ as Linkers or Counterions In Uranyl-Organic Species with cis- and trans-1,2-Cyclohexanedicarboxylate Ligands.

The macrocyclic species [Ni(cyclam)]2+ and [Ni(R,S-Me6cyclam)]2+ were used as addnl. cations in the solvo-hydrothermal synthesis of five uranyl ion complexes with cis- or trans-1,2-cyclohexanedicarboxylic acids (c-1,2-chdcH2 and t-1,2-chdcH2). In the complex [UO2(c-chdc)2Ni(cyclam)(H2O)] (1), dimeric uranyl dicarboxylate subunits are assembled into a two-dimensional (2D) network through axial coordination of NiII to carboxylate groups. Although they involve different isomers, the complexes [(UO2)2(c-chdc)2(c-chdcH)2Ni(cyclam)] (2) and [(UO2)2(t-chdc)2(t-chdcH)2Ni(cyclam)] (3) are very similar, both containing uranyl-based one-dimensional (1D) subunits which are assembled into 2D networks by bridging [Ni(cyclam)]2+ groups. The orientation of the uncoordinated carboxylic group is different in 2 and 3, the layers in 2 being hydrogen bonded to each other through carboxylic acid dimer formation. Using the pure (1R,2R) enantiomer of t-1,2-chdcH2 gives the complex [Ni(cyclam)][(UO2)5(R-t-chdc)3(R-t-chdcH)(O)2(CH3COO)] (4), in which pentanuclear uranyl subunits are assembled into 1D chains by dicarboxylic/-ate ligands in the usual bis(equatorial) chair conformation, another ligand in the divergent bis(axial) conformation uniting these chains into a 2D assembly; the [Ni(cyclam)]2+ ions are simple counterions and are stacked in parallel fashion between the layers. [Ni(R,S-Me6cyclam)][Ni(R,S-Me6cyclam)(H2O)2][(UO2)2(t-chdc)2(O)]2 (5), in which the (1R,2R) enantiomer of t-chdcH2 used has undergone racemization, contains discrete bis(μ3-oxo)-centered tetranuclear uranyl complexes, organized into columns and layers by extensive hydrogen bonding to the counterions. The discoidal shape, available axial coordination sites, and hydrogen bond donor potential of these macrocyclic NiII complexes make them efficient assembling agents in uranyl-organic coordination polymers. As often observed in the presence of d-block metal cations, uranyl luminescence is either completely or partially quenched in complexes 1 and 3, resp.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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 Synthesis and Antibacterial Activity of Novel (4-Methoxyphenyl)-tetrahydropyranyl-substituted 1,3,4-Oxadiazoles, published in 2020-04-30, which mentions a compound: 3326-71-4, Name is 2-Furoic hydrazide, Molecular C5H6N2O2, Synthetic Route of C5H6N2O2.

Condensation of 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonyl chloride I [R1 = Cl] with hydrazine hydrate, furan-2- and 2,5-dimethylfuran-2-carbohydrazides gave disubstituted hydrazides II [R2 = furan-2-carbonyl, (4,5-dimethylfuran-2-carbonyl), 4-(4-methoxyphenyl)tetrahydropyran-4-carbonyl], whose cyclization formed sym. and unsym. 2,5-disubstituted 1,3,4-oxadiazoles III [R3 = 2-furyl, 4,5-dimethyl-2-furyl, 4-(4-methoxyphenyl)tetrahydropyran-4-yl]. Et 4-[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carboxamido]benzoate IV [R4 = CO2Et] was reacted with hydrazine to obtain N-[4-(hydrazinocarbonyl)-phenyl]-4-(4-methoxphenyl)tetrahydro-2H-pyran-4-carboxamide IV [R4 = C(O)NHNH2]. Treatment of IV [R4 = C(O)NHNH2] latter with tri-Et orthoformate gave a monosubstituted 1,3,4-oxadiazole IV [R4 = 1,3,4-oxadiazol-2-yl], and with carbon disulfide, a 5-sulfanyl-1,3,4-oxadiazole derivative IV [R4 = (5-sulfanyl-1,3,4-oxadiazol-2-yl)] was obtained. The subsequent alkylation of this derivative IV [R4 = (5-sulfanyl-1,3,4-oxadiazol-2-yl)] with 5-metoxyfuran-2-Me and benzylaminocarbonylmethyl chlorides substituted chlorides resulted in the synthesis of the corresponding novel S-substituted oxadiazole derivatives V [R5 = 5-methoxycarbonyl-2-furyl, benzylcarbamoyl]. The synthesized compounds I, II, III, IV and V were tested for their antibacterial activity.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Category: benzisoxazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Stimulation of pollen tube growth in vitro by dicarboxylic acids. Author is Iwanami, Y..

At 50 ppm, capric acid [334-48-5] and 2-decenoic acid [3913-85-7] almost totally inhibited the germination of Camellia japonica pollen. Moderate inhibition was shown by traumatic acid [6402-36-4], caprylic acid [124-07-2], and IAA [87-51-4]. The above compounds also inhibited pollen tube elongation. At 10 ppm, oxalic acid [144-62-7], succinic acid [110-15-6], suberic acid [505-48-6], adipic acid [124-04-9], sebacic acid [111-20-6], cis-1,2-cyclohexanedicarboxylic acid [610-09-3], and 3,3-diethylglutaric acid [4160-95-6] stimulated pollen tube elongation.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Safety of cis-Cyclohexane-1,2-dicarboxylic acid. 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: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Probing Single-Chain Magnets in a Family of Linear Chain Compounds Constructed by Magnetically Anisotropic Metal-Ions and Cyclohexane-1,2-Dicarboxylate Analogues. Author is Zheng, Yan-Zhen; Xue, Wei; Tong, Ming-Liang; Chen, Xiao-Ming; Zheng, Shao-Liang.

Five new metal-carboxylate chain-based laminated compounds, namely, ∞2[FeII(e,e-trans-1,2-chdc)] (3) (1,2-chdc = cyclohexane-1,2-dicarboxylate), ∞2[NiII(μ-OH2)(e,a-cis-1,2-chdc)] (4), ∞2[CoII(μ-OH2)(1,2-chedc)] (5) (1,2-chedc = cyclohex-1-ene-1,2-dicarboxylate), ∞2[CoII5(μ3-OH)2(OH2)2(1,2-chedc)4] (6), and ∞2[CoII(4-Me-1,2-chdc)] (7) (4-Me-1,2-chdc = trans-4-methylcyclohexane-1,2-dicarboxylate) were hydrothermally synthesized. In these series of magnetic chain-based compounds, 3 and 7 have the same dimeric paddle-wheel M(II)-carboxylate chain as the previously reported compound, ∞2[CoII(trans-1,2-chdc)] (2). However, compound 3 does not behave as a single-chain magnet (SCM) but simply an alternating ferro-antiferro magnetic chain. Compound 4 has the cis conformation of 1,2-chdc ligand, which leads to a uniform aqua-carboxylate-bridged Ni(II) chain. Such a Ni-O chain exhibits strong antiferromagnetic interactions, leading to a diamagnetic ground state. Compound 5 features a corner-sharing triangular chain, or Δ-chain, which is part of a Kagome lattice. However, 5 does not exhibit a spin-frustrated effect but simply spin competition. Compound 6 has a unique pentanuclear CoII cluster, which is further connected by the syn-anti carboxylate into a chain structure. Compound 6 exhibits antiferromagnetic interactions among the Co(II) ions, and no SCM behavior is observed These results might indicate that the dimeric paddle-wheel Co(II)-carboxylate chain is essential in obtaining SCM behavior in this family of compounds Although 2 and 7 have very similar SCM behavior, a.c. magnetic studies show that 7 has a higher energy barrier than that of 2. Such behavior is probably caused by the larger anisotropic energy barrier in 7.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrogenation of aromatic compounds with the aid of platinum. III. Hydrogenation with platinum containing oxygen》. Authors are Willstatter, Richard; Jaquet, Daniel.The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).SDS of cas: 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cf. C. A. 7, 1508. Certain reductions, like that of phthalic anhydride (a), which cannot be effected catalytically with Pt free from O, can be initiated by loading the Pt with O and brought to completion by again treating the Pt with O as the catalyst gradually loses its O by the formation of H2O. Oxygen-free Pt and that containing O behave like 2 different contact substances in reduction processes. Thus, 20.3 g. (a) in 75 cc. glacial AcOH with 5 g. Pt absorbed only 400 cc. H; if, however, the H gasometer was shut off and the reaction bulb evacuated, then allowed to fill with air, shaken 1 min. (whereupon O was rapidly absorbed -about 5 cc. per g. Pt) and the air was driven out with H, about 500 cc. of H was again absorbed after each such activation until the 20th and 21st times, when the absorption of H was 1230 and 5600 cc., rasp. The total absorption was 17040 cc. (20°, 760 mm.) or, deducting about 1150 cc. used up by the O introduced in the activations, 15890 cc. or 4.8 mols. Of the 2 rings in (a) the 5-membered one is reduced before the C6H6 ring; the first product is phthalide (b) which is partially reduced to hexahydrophthalide (c) and partially to o-MeC6H4CO2H (d) which is then reduced to the hexahydrotoluic acid (e). If the process is interrupted when only a little H has been absorbed there is obtained, besides some C6H6(CO2H)2, a mixture of (b) and (c), and while (b) is easily reduced further to (d), (c) cannot be reduced to (e). If in the process of isolation alkali is employed the (c) is in part obtained as methylolhexahydrobenzoic acid. Among the reduction products is also cis-hexahydrophthalic acid (f). In the reduction described above were obtained 7 g. (c) (partially hydrolyzed), 7 g. (e) and 4 g. (f). In a similar reduction of (b) 3.4 mols. H were absorbed and there were obtained about equal parts of (e) and (c). Phthalimide behaves quite differently from (a) on reduction, the aromatic nucleus and not the CO groups taking up the O. The activation of the Pt with O is not necessary but the reduction is successful only with the best Pt sponge preparations; many which were active towards C6H6 were inactive towards the imide. Nor can MeOH, EtOH or cyclohexane be used as a solvent; in glacial AcOH the reduction proceeds smoothly. cis-Hexahydrophthalimide seps. from H2O, alc. and AcOH in monoclinic prisms, m. 132°. Naphthalic acid purified by crystallization from alc. cannot be reduced because it always contains some anhydride (g) but the acid freshly precipitated from alk. solution can be reduced; contrary to C10H8, it takes up only 4 atoms of H; the tetrahydronaphthalic acid (h) seps. in cube-like prisms, m. 196° with loss of H2O and conversion into the anhydride, m. 119°. (g), like (a), can be reduced only with Pt activated with O; after about 4 mols. H2 have been absorbed the reaction slows up. As far as the (g) itself is reduced, the anhydride ring is attacked, but as some of the (g) is hydrolyzed by the H2O formed, some (h) is obtained. Among the reduction products are tetrahydro-1-methylnaphthalene-8-carboxylic acid (i), tetra- and decahydronaphthalides and a small amount of decahydroacenaphthene. The 2 naphthalides could not be isolated pure. The (i) seps. from Et2O-petr. ether in needles, m. 150°. o-C6H4(CO2H)2 is easily reduced in AcOH when entirely free from the anhydride, yielding exclusively the cis-hexahydro acid, m. 191-2°. The p-acid in AcOH suspension is reduced much more rapidly on gentle warming, giving about equal parts of the cis- and cis-trans-hexahydro acids, m. 162-3° and about 300°, resp. The m-acid, if pure, is likewise easily reduced in AcOH suspension, forming chiefly the cis- and some cis-trans-hexahydro acid. p-Toluylic acid very quickly gives exclusively or almost exclusively the liquid hexahydro acid whose amide m. 175-6°. Indole in AcOH smoothly absorbs 8 atoms H with formation of perhydroindole, b720 182-3°, b12 65°, a basic oil of medium consistency and unpleasant, penetrating, onion-like odor, d420 0.9947; chloroplatinate, reddish yellow monoclinic tablets from alc., m. 172-3° (not sharply); picrate, fine needles from alc., m. 137-8° (not sharply). If the reduction is interrupted before it is complete (e. g., when 2 atoms of H have been absorbed), the product contains unchanged indole, dihydroindole and perhydroindole, the last being removed by shaking the Et2O solution with 0.1 N HCl until the alk. reaction just disappears, and the first two being separated by fractional precipitation from Et2O with picric acid.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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.Chethan Prathap, K. N.; Shalini, P.; Lokanath, N. K. researched the compound: 2-Furoic hydrazide( cas:3326-71-4 ).Recommanded Product: 2-Furoic hydrazide.They published the article 《Synthesis, characterization, crystal structure, Hirshfeld surface analysis and DFT calculations of two novel pyrrole derivatives》 about this compound( cas:3326-71-4 ) in Journal of Molecular Structure. Keywords: pyrrolylethylidene benzenesulfonohydrazide diastereoselective preparation crystal structure Hirshfeld surface analysis; furancarbohydrazide ethylidenepyrrole diastereoselective preparation crystal structure Hirshfeld surface analysis. We’ll tell you more about this compound (cas:3326-71-4).

The novel pyrroles (E)-N’-(1-(1H-pyrrol-2-yl)ethylidene)benzenesulfonohydrazide and (E)-N’-(1-(1H-pyrrol-2-yl)ethylidene)furan-2-carbohydrazide were synthesized. The synthesized comps. were characterized by (1H and 13C) NMR, FT-IR, UV-visible, TG-DTA and XRD studies.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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 DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles, published in 2019, which mentions a compound: 3326-71-4, mainly applied to DMF aryl hydrazide copper catalyst oxidative heterocyclization green chem; aryl oxadiazole preparation oxygen copper catalyst oxidation green chem; oxadiazolone aryl preparation, Product Details of 3326-71-4.

An unprecedented Cu-catalyzed direct annulation of hydrazides with N,N-dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4-oxadiazoles. This process featured short reaction time and safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4-oxadiazole-2(3H)-ones. Moreover, the mechanistic studies suggested that the source of CH was from the N-Me group of DMF.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics