Heterocyclic Building Blocks-Benzisoxazole

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).Application of 610-09-3. 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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Furoic hydrazide( cas:3326-71-4 ) is researched.Quality Control of 2-Furoic hydrazide.Haribabu, Jebiti; Srividya, Swaminathan; Umapathi, Reddicherla; Gayathri, Dasararaju; Venkatesu, Pannuru; Bhuvanesh, Nattamai; Karvembu, Ramasamy published the article 《Enhanced anticancer activity of half-sandwich Ru(II)-p-cymene complex bearing heterocyclic hydrazone ligand》 about this compound( cas:3326-71-4 ) in Inorganic Chemistry Communications. Keywords: cymene ruthenium indole hydrazone preparation crystal mol structure; anticancer half sandwich ruthenium cymene heterocyclic hydrazone complex. Let’s learn more about this compound (cas:3326-71-4).

The hydrazone ligand (HL) was synthesized from furan-2-carbohydrazide and indole-3-carboxaldehyde. The reaction of [RuCl2(p-cymene)]2 with HL in the presence of sodium methoxide yielded organometallic Ru(II)-p-cymene compound of the type [RuCl(η6-p-cymene)(η2-N,O-indole hydrazone)] (1). The ligand and complex were characterized by CHN anal. and various spectroscopic tools. The piano stool (pseudo-octahedral) geometry of the complex was confirmed by single crystal x-ray diffraction. The anticancer property of the ligand and complex was investigated against A549, HeLa and MCF7 cancer cell lines. The complex exhibited superior activity against A549 and HeLa cancer cells with the IC50 values of 23.4 and 12.9μM, resp.

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Synthetic stratagem, characterization and biocidal applications of triorganotin(IV) complexes derived from hydrazide/hydrazone analogues, the main research direction is triorganotin benzylidene benzohydrazide preparation antibacterial antifungal antidiabetic activity; alpha amylase inhibitor triorganotin benzylidene benzohydrazide complex; furanylmethylene furancarbohydrazide preparation crystal mol structure.COA of Formula: C5H6N2O2.

A series of Schiff base ligands as benzylidene benzohydrazide and their hydrazone analogs (Ia-Ic) have been synthesized and then complexed with organotin(IV) moiety having general formula [R’3SnL] to get the target compounds (1-9), where L = C4H3OCONHN:CHR, R = C6H5O (Ia), C4H5O (Ib), C6H3Cl2 (Ic) and R’ = -CH3 (1-3), -CH2Ph (4-6), -Ph (7-9). They were fully characterized using FT-IR, NMR (1H, 13C and 119Sn) spectroscopy, along with elemental anal. and m.p. One of the precursor (Ib) has been analyzed by single crystal XRD to further authenticate the structure. The 119Sn NMR data suggest the mol. geometry of organotin derivatives as distorted pentagonal bipyramidal. They were also evaluated for their antibacterial, antifungal, α-amylase inhibition, DPPH, total reducing power and total antioxidant activities. Triaryltin(IV) derivatives show good antibacterial and antifungal activity. Whereas the data for antidiabetic activity demonstrated that the compounds may serve as moderately effective alpha amylase inhibitor.

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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, Russian Journal of General Chemistry called Photoconductivity, Antioxidant, and Antimicrobial Activities of Some Acenaphthenequinone Derivatives, Author is Mhaidat, I.; Taha, Z. A.; Al Momani, W.; Hijazi, A. K., which mentions a compound: 3326-71-4, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2, Category: benzisoxazole.

Photoconductive acenaphthenequinone derivatives I (R = thiophen-2-yl, 3-hydroxynaphthalen-2-yl, pyridin-4-yl, etc.) have been synthesized by a one-pot process of acenaphthenequinone with different aromatic hydrazides RC(O)NHNH2. Photoelectrochem. (PEC) measurements reveal that the compounds demonstrate photoresponse upon illumination by light of intensities 1000 and 10000 W/m2. The photoconductivity behavior of the derivatives I is enhanced in the presence of electron donor groups attached to the aromatic ring. Thereby, these products may be used in material devices as organic thin film transistors, on/off sensors, etc. The antioxidant activity of the products has been tested by DPPH radical scavenging method in vitro, indicating their significant potential. Antimicrobial activity of the derivatives I has been estimated by min. inhibitory concentration (MIC, mg/mL) using the micro-broth dilution method. The compounds are moderately active against some Gram pos. bacteria and Candida albicans and completely inactive against Gram neg. bacteria tested.

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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.Muller, Giel; Scheer, Adam; Osborn, David L.; Taatjes, Craig A.; Meloni, Giovanni researched the compound: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8 ).Formula: C6H10O3.They published the article 《Low Temperature Chlorine-Initiated Oxidation of Small-Chain Methyl Esters: Quantification of Chain-Terminating HO2-Elimination Channels》 about this compound( cas:37443-42-8 ) in Journal of Physical Chemistry A. Keywords: small chain methyl ester low temperature chlorine initiated oxidation. We’ll tell you more about this compound (cas:37443-42-8).

Cl-initiated oxidation reactions of three small-chain Me esters, Me propanoate (CH3CH2COOCH3; MP), Me butanoate (CH3CH2CH2COOCH3; MB), and Me valerate (CH3CH2CH2CH2COOCH3; MV), are studied at 1 or 8 Torr and 550 and 650 K. Products are monitored as a function of mass, time, and photoionization energy using multiplexed photoionization mass spectrometry coupled to tunable synchrotron photoionization radiation. Pulsed photolysis of mol. chlorine is the source of Cl radicals, which remove an H atom from the ester, forming a free radical. In each case, after addition of O2 to the initial radicals, chain-terminating HO2-elimination reactions are observed to be important. Branching ratios among competing HO2-elimination channels are determined via absolute photoionization spectra of the unsaturated Me ester coproducts. At 550 K, HO2-elimination is observed to be selective, resulting in nearly exclusive production of the conjugated Me ester coproducts, Me propenoate, methyl-2-butenoate, and methyl-2-pentenoate, resp. However, in MV, upon raising the temperature to 650 K, other HO2-elimination pathways are observed that yield Me 3-pentenoate and Me 4-pentenoate. In each Me ester oxidation reaction, a peak is observed at a mass consistent with cyclic ether formation, indicating chain-propagating OH loss/ring formation pathways via QOOH intermediates. Evidence is observed for the participation of resonance-stabilized QOOH in the most prominent cyclic ether pathways. Stationary point energies for HO2-elimination pathways and select cyclic ether formation channels are calculated at the CBS-QB3 level of theory and assist in the assignment of reaction pathways and final products.

Compounds in my other articles are similar to this one(Methyl tetrahydrofuran-2-carboxylate)Formula: C6H10O3, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.

Reference:
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 Zinc(II) and cadmium(II) complexes with mixed 1,3-di(1H-imidazol-4-yl)benzene and cyclohexanedicarboxylate ligands: Synthesis, structure and property. Author is Chen, Zhi-Hao; Zhao, Yue; Wang, Peng; Chen, Shui-Sheng; Sun, Wei-Yin.

Eight new coordination polymers Zn(L)(cis-1,2-CHDA)| (1), Zn(L)(trans-1,3-CHDA)|·2.5H2O (2), Zn(L)(cis-1,3-CHDA)|·H2O (3), Cd(L)(cis-1,2-CHDA)|·3H2O (4), Cd2(L)2(cis-1,2-CHDA)2|·3H2O (5), Cd(L)(cis-1,3-CHDA)|·H2O (6), Cd(L)(cis-1, 4-CHDA)|·5H2O (7) and Cd(L)(cis-1,4-CHDA)| (8) were synthesized by reactions of corresponding metal salt with 1,3-di(1H-imidazol-4-yl)benzene (L) and different carboxylic acids such as 1,2-cyclohexanedicarboxylic acid (1,2-H2CHDA), 1,3-cyclohexanedicarboxylic acid (1,3-H2CHDA) and 1,4-cyclohexanedicarboxylic acid (1,4-H2CHDA), resp. The results of crystal structure anal. revealed that 4, 7 and 8 are chains, 1, 3, 5 and 6 are (3)-connected 2D networks with Point (Schlaefli) symbol of (63), while 2 is a (3,3)-connected 2D network with Point (Schlaefli) symbol of (44,62). Thermal stability and photoluminescence of the complexes were investigated. Furthermore, DFT calculations were carried out on 2-5, and 7 and 8 to discuss the temperature dependent reaction of the complexes.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Furoic hydrazide( cas:3326-71-4 ) is researched.Computed Properties of C5H6N2O2.Dige, Nilam C.; Mahajan, Prasad G.; Raza, Hussain; Hassan, Mubashir; Vanjare, Balasaheb D.; Hong, Hansol; Hwan Lee, Ki; Latip, Jalifah; Seo, Sung-Yum published the article 《Ultrasound mediated efficient synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as potent tyrosinase inhibitors: Mechanistic approach through chemoinformatics and molecular docking studies》 about this compound( cas:3326-71-4 ) in Bioorganic Chemistry. Keywords: oxoquinazolinyl furancarboxamide green preparation tyrosinase inhibitor chemoinformatic docking antioxidant; isatoic anhydride furoic hydrazide salicylaldehyde acid catalyst ultrasound irradiation; Drug score; Lipinski’s rule; Molecular docking; Oxoquinazolin-3(4H)-yl)furan-2-carboxamides; Tyrosinase; Ultrasound sonication. Let’s learn more about this compound (cas:3326-71-4).

Synthesis of new (4-oxoquinazolin-3(4H)-yl)furan-2-carboxamide derivatives I [R = H, 5-Br, 3-NO2, etc.] via p-TSA catalyzed reaction between isatoic anhydride, 2-furoic hydrazide and substituted salicylaldehydes in ethanol:water (5:5 volume/volume) solvent system under ultrasound irradiation at room temperature was carried out. The important features of this protocol were simple and easy workup procedure, reaction carried out at ambient temperature, use of ultrasound and high yield of (4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides in short reaction time. The synthesized compounds I were screened against tyrosinase enzyme and all these compounds found to be potent inhibitors with much lower IC50 value of 0.028 ± 0.016 to 1.775 ± 0.947 μM than the standard kojic acid (16.832 ± 1.162 μM). The kinetics mechanism for compound I [R = 3,5-di-Br] was analyzed by Lineweaver-Burk plots which revealed that compound inhibited tyrosinase non-competitively by forming an enzyme-inhibitor complex. Along with this all the synthesized compounds I were scanned for their DPPH free radical scavenging ability. The outputs received through in vitro and in silico anal. were coherent to the each other with good binding energy values (kcal/mol) posed by synthesized ligands.

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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 《Stereochemistry of cyclic compounds. 1,3-Cyclopentenedione in Diels-Alder reaction》. Authors are Kucherov, V. F.; Ivanova, L. I..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.

Oxidation of 1,3-cyclopentenediol with CrO3 in AcOH with ice cooling gave 26% 1,3-cyclopentenedione (I), b1 60°, n20D 1.5045, m. 35-6°, after cooling. The dione condenses readily with butadiene in C6H6 (pyrogallol added) in 2 weeks at room temperature to yield cis-Δ5-hexahydroindene-1,3-dione, m. 157.5-8.5°; hydrogenation over Pd gave 1,3-hydrindandione, m. 86-6.5°, which with Br2-NaOH gave cis-1,2-cyclohexanedicarboxylic acid, m. 186.5-7.5°. I condensed with isoprene in C6H6 to the adduct, 5-methyl-Δ5-hexahydroindene-1,3-dione, m. 84.5-5.5°. Cyclopentadiene gave the adduct, C10H10O2, m. 178-8.5°, which hydrogenated over Pd to endomethylenehydrindan-1,3-dione, m. 166-6.5°. I and 1-vinylcyclohexene gave the adduct, 4,5-tetramethylene-Δ5-hexahydroindene-1,3-dione, m. 120-1°. I and 6-methoxy-1-vinyl-Δ3,4-dihydronaphthalene similarly gave in 1 day at room temperature II, m. 206.5-7.5°.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: cis-Cyclohexane-1,2-dicarboxylic acid( cas:610-09-3 ) is researched.Related Products of 610-09-3.Salakhov, M. S.; Israfilov, A. I.; Gulieva, R. S.; Mamedov, S. A. published the article 《Analysis of the stereochemistry of cyclic dicarboxylic acids by potentiometric titration. IX. Acidic ionization of stereoisomeric cyclic 1,2-dicarboxylic acids in aqueous methanol mixtures》 about this compound( cas:610-09-3 ) in Voprosy Stereokhimii. Keywords: acidity cyclic diacid stereoisomer. Let’s learn more about this compound (cas:610-09-3).

The ionization constants of I-V were determined at 25° for potentiometric titration The cis acids were weaker than the trans acids, and the saturated acids were weaker than the unsaturated ones. The distance between ionizing carboxyls in cis-trans pairs, as calculated by the Ingold method, was apparently the same.

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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 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives with anti-acetylcholinesterase activities, published in 2021, which mentions a compound: 3326-71-4, mainly applied to diethylaminocoumarinyl oxadiazole preparation acetylcholinesterase inhibition SAR docking; 1,3,4-oxadiazole; Coumarin; acetylcholinesterase inhibitor; molecular docking, COA of Formula: C5H6N2O2.

Twelve novel 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives I [R = n-Bu, 2-thienyl, Ph, etc.] were synthesized via iodine-mediated oxidative cyclization and confirmed by 1H NMR, 13C NMR and HRMS. The synthesized derivatives I were tested against in-vitro acetylcholinesterase inhibitory activity and results showed that compounds I [R = 4-ClC6H4, 4-BrC6H4] exhibited moderate inhibitory activities with 69.19% and 65.06%, resp. The preliminary structure-activity relationships revealed that introduction of halogen atom on the para-position of Ph of compounds I could enhance their activities. Mol. docking study suggested that compound I [R = ClC6H4] possessed an optimal docking pose with interactions inside AChE.

Compounds in my other articles are similar to this one(2-Furoic hydrazide)COA of Formula: C5H6N2O2, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.

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