Heterocyclic Building Blocks-Benzisoxazole

Recommanded Product: 3326-71-4. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Binucleating Hydrazonic Ligands and Their μ-Hydroxodicopper(II) Complexes as Promising Structural Motifs for Enhanced Antitumor Activity. Author is Rada, Jesica Paola; Bastos, Beatriz S. M.; Anselmino, Luciano; Franco, Chris H. J.; Lanznaster, Mauricio; Diniz, Renata; Fernandez, Claudio O.; Menacho-Marquez, Mauricio; Percebom, Ana Maria; Rey, Nicolas A..

Very few inorganic antineoplastic drugs have entered the clinic in the last decades, mainly because of toxicity issues. Because Cu is an essential trace element of ubiquitous occurrence, decreased side effects could be expected in comparison with the widely used Pt anticancer compounds Two novel hydrazonic binucleating ligands and their μ-hydroxo dicopper(II) complexes were prepared and fully characterized. They differ by the nature of the aromatic group present in their aroylhydrazone moieties: while H3L1 and its complex [Cu2(μ-OH)(HL1)](ClO4) (1), possess a thiophene ring, H3L2 and [Cu2(μ-OH)(HL2)](ClO4) (2) contain the more polar furan heterocycle. X-ray diffraction indicates that both coordination compounds are very similar in structural terms and generate dimeric arrangements in the solid state. Pos.-ion electrospray ionization mass spectrometry analyses confirmed that the main species present in a 10% DMSO/water solution should be [Cu2(HL)(OH)]+ and the DMSO-substituted derivative [Cu2(L)(DMSO)]+. Scattering techniques [dynamic light scattering (DLS) and small-angle x-ray scattering] suggest that the complexes and their free ligands interact with bovine serum albumin (BSA) in a reversible manner. The binding constants to BSA were determined for the complexes through fluorescence spectroscopy. Also, to gain insight into the mechanism of action of the compounds, calf thymus DNA binding studies by UV-visible and DLS measurements using plasmid pBR322 DNA were also performed. For the complexes, DLS data seem to point to the occurrence of DNA cleavage to Form III (linear). Both ligands and their dicopper(II) complexes display potent antiproliferative activity in a panel of four cancer cell lines, occasionally even in the submicromolar range, with the complexes being more potent than the free ligands. The authors’ data on cellular models correlate quite well with the DNA interaction experiments The results presented herein show that aroylhydrazone-derived binucleating ligands, as well as their dinuclear μ-hydroxodicopper(II) complexes, may represent a promising structural starting point for the development of a new generation of highly active antitumor agents.

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Reference:
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 《Application of the cyano ester ring closure to five- and six-membered rings》. Authors are Fuson, Reynold C.; Cole, Wayne.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).Quality Control of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cf. F. and Kao, C. A. 23, 2424. Et α,α’-dibromopimelate and KCN in absolute EtOH, refluxed for 60 hrs., give 80-8% of Et 1-cyano-1,2-cyclopentanedicarboxylate, b2 126-8°, d420 1.108, nD20 1.4560; hydrolysis with concentrated HCl gives a mixture of trans- and cis-1,2-cyclopentanedicarboxylic acid (Perkins, J. Chem. Soc. 65, 572(1894)). Similarly Et α,α’-dibromosuberate yields 48-55% of Et 1-cyano-1,2-cyclohexanedicarboxylate, b2 129-30°, d420 1.082, nD20 1.4570; hydrolysis with 20% HCl yields a mixture of the 2 1,2-cyclohexanedicarboxylic acids, the trans-isomer being obtained pure (Baeyer, Ann. 258, 213(1890)). Et α,α’-dibromoazelate and Et α,α’-dibromosebacate failed to give detectable quantities of the cyclic CN esters containing 7- or 8-membered rings.

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

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, Polyhedron called Nitroaromatic detecting zinc cyclohexyldicarboxylate coordination polymers with a long spanning dipyridyl tethering ligand, Author is LaDuca, Andrew R.; Przybyla, Jack J.; Porta, Angela R.; LaDuca, Robert L., which mentions a compound: 610-09-3, SMILESS is O=C([C@H]1[C@@H](C(O)=O)CCCC1)O, Molecular C8H12O4, Reference of cis-Cyclohexane-1,2-dicarboxylic acid.

Four new divalent Zn coordination polymers containing a dianionic cyclohexyldicarboxylate and the long-spanning pillaring dipyridyl ligand bis(4-pyridylmethyl)piperazine (bpmp) were prepared and structurally characterized via single-crystal x-ray diffraction. Significant structural and topol. diversity across the series is evident. {[Zn2(cis-12cdc)2(bpmp)]·6H2O}n (1, cis-12cdc = cis-1,2-cyclohexanedicarboxylate) shows a coordination polymer layer motif with embedded paddlewheel {Zn2(OCO)4} dinuclear units and T6(4)4(4) classification H2O tapes. Using cis-1,2-cyclohex-4-enedicarboxylate (cis-12chedc) afforded [Zn2(cis-12chedc)2(bpmp)(H2O)2]n (2), which manifests a simple yet unusual (6)(648.10) topol. [Zn2(cis-13cdc)2(bpmp)]n (3, cis-13cdc = cis-1,3-cyclohexanedicarboxylate) displays sawtooth (4,4) coordination polymer layers, while [Zn2(trans-14cdc)2(bpmp)]n (4, trans-14cdc = trans-1,4-cyclohexanedicarboxylate) shows a 3-dimensional system of coordination polymer networks with 3-fold interpenetrated 41263pcu topol. The layered phases 1-3 showed capability for the detection of small quantities of nitrobenzene in EtOH suspension.

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Reference:
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 《The configuration of polymethylenedicarboxylic acids. I. The dissociation constants of the cyclohexanedicarboxylic acids》. Authors are Kuhn, Richard; Wassermann, Albert.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).Formula: C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

The 1st and 2nd dissociation constants for the cyclohexanedicarboxylic acids in water and in 50% MeOH are given as follows (-log K, -log K2 and K1/K2, resp.): In H2O: o-cis, 4.34 (19°), 6.76 (19°), 267; o-trans, 4.18 (18°), 5.93 (19°), 56; m-cis, 4.10 (16°), 5.46 (16°), 23; m-trans, 4.31 (19°), 5.73 (19°), 26; p-cis, 4.44 (20°), 5.79 (19°), 22; p-trans, 4.18 (16°), 5.42 (19°), 17. In 50% MeOH: o-cis, 5.26 (18°), 8.20 (18°), 885; o-trans, 5.38 (18°), 7.31 (18°), 85; m-cis, 5.25 (17°), 6.83 (17°), 38; m-trans, 5.48 (19°), 7.40 (19°), 83; p-cis, 5.59 (19°), 7.15 (19°), 36; p-trans, 5.32 (18°), 6.81 18°), 30. The configurations of the various isomeric forms of the hexahydrophthalic acids are graphically presented.

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

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: 610-09-3, is researched, SMILESS is O=C([C@H]1[C@@H](C(O)=O)CCCC1)O, Molecular C8H12O4Journal, Article, Research Support, Non-U.S. Gov’t, Inorganic Chemistry called 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, the main research direction is transition metal cyclohexane carboxylate polymer complex magnetic preparation structure; crystal structure transition metal cyclohexane carboxylate polymer complex; magnetic property transition metal cyclohexane carboxylate polymer complex.Recommanded Product: 610-09-3.

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

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, Non-U.S. Gov’t, Organic Letters called Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols, Author is Thiyagarajan, Subramanian; Gunanathan, Chidambaram, which mentions a compound: 3326-71-4, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2, Reference of 2-Furoic hydrazide.

Herein, direct N,N-dialkylation of acylhydrazides using alcs. is reported. This catalytic protocol provides one-pot synthesis of both sym. and unsym. N,N-disubstituted acylhydrazides using an assortment of primary and secondary alcs. with remarkable selectivity and excellent yields. Interestingly, the use of diols resulted in intermol. cyclization of acylhydrazides, and such products are privileged structures in biol. active compounds Water is the only byproduct, which makes this catalytic protocol sustainable and environmentally benign.

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

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, European Journal of Organic Chemistry called Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions, Author is Lu, Fangling; Gong, Fengping; Li, Liangsen; Zhang, Kan; Li, Zhen; Zhang, Xinwei; Yin, Ying; Wang, Ying; Gao, Ziwei; Zhang, Heng; Lei, Aiwen, which mentions a compound: 3326-71-4, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2, Formula: C5H6N2O2.

1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive mols. In this study, intermol. electrochem. cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91% [e.g., benzohydrazide + 2-oxo-2-phenylacetic acid → 2,5-diphenyl-1,3,4-oxadiazole (90%)]. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both sym. and unsym. 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation

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

Related Products of 610-09-3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about Reductive metabolism and its role in the disposition of the hydroxamic angiotensin-converting enzyme inhibitor idrapril calcium in rat. Author is Lippi, A.; Criscuoli, M.; Canali, S.; Subissi, A..

The metabolism of 14C-idrapril calcium, the prototype of a new class of angiotensin-converting enzyme inhibitors, was studied in rat after a single i.v. administration. Plasma, urine, feces, and bile were assayed for total and HPLC-fractionated radioactivity. Only one major metabolite (M1, 2-sarcosinamide-cis-1,2-cyclohexanedicarboxylamide) was observed, along with idrapril, in plasma. Three metabolites (M1, M2, cis-1,2-cyclohexanedicarboxylic acid, and M3, and glucuronate derivative of M1) were present in 0-8-h urine, unchanged idrapril being the most abundant product. In bile, two metabolites (M1, M3), but not the parent compound, were found. In conclusion i.v. idrapril undergoes hepatic reduction to M1 and hydrolysis to M2. M1 can be glucuronated to M3 and both are partially excreted in the bile and further processed in the gut to reabsorbable radioactive species.

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Reference:
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 《The kinetics of the acid-catalyzed hydrolysis of the methyl esters of cyclohexanedicarboxylic acids》. Authors are Smith, Hilton A.; Scrogham, Kenneth G.; Stump, Billy L..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).COA of Formula: C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Isomeric cyclohexane dicarboxylic acids (I) were made by reduction of phthalic acids: cis-1,2 (II), m. 194°; trans-1,2 (III), m. 227.5-9.4°; cis-1,3 (IV), m. 167.2-8.2°; cis-1,4 (V), m. 170-2°; and trans-1,4 (VI), m. 312-13°. Di-Me esters made by acid-catalyzed esterification with MeOH were: II, b12 124.4°; III, m. 30.2-30.8°; V, b10 131°; and VI, m. 69°. IV di-Me ester, b10 130.6°, was made from the Ag salt and MeI, whereas trans-1,3-di-Me ester (VII), b20 140°, was made from H and 1,3-C6H4(CO2Me)2 with Adams Pt catalyst. Mono-Me derivative of II, m. 68.5-9.0°, was made similarly from 2-HO2CC6H4CO2Me and H. Mono-Me derivative of III, m. 94.5-95°, was made from the acid and MeOH. Mono-Me derivative of IV, m. 66.2-7.0°, was made from the acid chloride and MeOH. By treatment of the di-Me esters with 1 equivalent KOH, mono-Me derivative of V, m. 106.6-8.6°, mono-Me derivative of VI, m. 125.6-6.8°, and mono-Me derivative of trans-1,3-I were prepared Acid-catalyzed rate constants for these esters were determined at 25°, 35°, 45°, and 55° and the heats of activation calculated Me and di-Me esters of II and III hydrolyzed most slowly, those of IV and VI most rapidly, and those of V and VII at an intermediate rate.

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

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Solid-phase synthesis of hybrid 2,5-diketopiperazines using acylhydrazide, carbazate, semicarbazide, amino acid, and primary amine submonomers.Application of 3326-71-4.

46We report the solid-phase synthesis of N,N’-di(acylamino)-2,5-diketopiperazine, an acylhydrazide-based conformationally rigid 2,5-DKP scaffold having exocyclic N-N bonds. We also show that different combinations of acylhydrazides, carbazates, semicarbazides, amino acids, and primary amines can be used to synthesize a highly diverse collection of hybrid DKP mols. via the solid-phase submonomer synthesis route. Finally, we show incorporation of a Me substituent in one of the carbon atoms of the DKP ring to generate chiral daa- and hybrid-DKPs without compromising the synthetic efficiency.

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