Tag: M.W:100-200

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: 27231-36-3, is researched, SMILESS is SC1=NC2=CC(C)=CC=C2N1, Molecular C8H8N2SJournal, Article, Research Support, Non-U.S. Gov’t, Scientific Reports called Novel giardicidal compounds bearing proton pump inhibitor scaffold proceeding through triosephosphate isomerase inactivation, Author is Hernandez-Ochoa, B.; Navarrete-Vazquez, G.; Nava-Zuazo, C.; Castillo-Villanueva, A.; Mendez, S. T.; Torres-Arroyo, A.; Gomez-Manzo, S.; Marcial-Quino, J.; Ponce-Macotela, M.; Rufino-Gonzalez, Y.; Martinez-Gordillo, M.; Palencia-Hernandez, G.; Esturau-Escofet, N.; Calderon-Jaimes, E.; Oria-Hernandez, J.; Reyes-Vivas, H., the main research direction is Giardia antiparasitic giardicidal compound proton pump inhibitor triosephosphate isomerase.Synthetic Route of C8H8N2S.

Giardiasis is a worldwide parasitic disease that affects mainly children and immunosuppressed people. Side effects and the emergence of resistance over current used drugs make imperative looking for new antiparasitics through discovering of new biol. targets and designing of novel drugs. Recently, it has determined that gastric proton-pump inhibitors (PPI) have anti-giardiasic activity. The glycolytic enzyme, triosephosphate isomerase (GlTIM), is one of its potential targets. Therefore, we employed the scaffold of PPI to design new compounds aimed to increase their antigiardial capacity by inactivating GlTIM. Here we demonstrated that two novel PPI-derivatives (BHO2 and BHO3), have better anti-giardiasic activity than omeprazole in concentrations around 120-130 muM, without cytotoxic effect on mammal cell cultures. The derivatives inactivated GlTIM through the chem. modification of Cys222 promoting local structural changes in the enzyme. Furthermore, derivatives forms adducts linked to Cys residues through a C-S bond. We demonstrated that PPI can be used as scaffolds to design better antiparasitic mols.; we also are proposing a mol. mechanism of reaction for these novel derivatives

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Carbateas, P. M.; Williams, Gordon L. published the article 《Two methods for conversion of an aromatic aldehyde to a 4-arylpyridine. A method for preparation of 3-alkyl-4-arylpyridines》. Keywords: pyridine nitrophenyl; methylpyridine nitrophenyl; nitrophenylpyridine.They researched the compound: 1-(Furan-2-yl)propan-1-one( cas:3194-15-8 ).Application In Synthesis of 1-(Furan-2-yl)propan-1-one. 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:3194-15-8) here.

Reaction of 1-(2-furyl)-3-(m-nitrophenyl)propenone with 2-acetylfuran (I) and NH4OAc in AcOH at reflux gave 2,6-di(2-furyl)-4-(m-nitrophenyl)pyridine, which was oxidized with dilute HNO3 and the resultant 4-(m-nitrophenyl)-2,6-pyridinedicarboxylic acid decarboxylated by heating with Dowtherm to give 4-(m-nitrophenyl)pyridine (II). II was alternatively prepared by heating a mixture of m-O2NC6H4CHO, CHCCO2Me, and NH4OAc in AcOH at reflux, oxidizing the product (III) with dil HNO3, hydrolyzing the resultant di-Me 4-(m-nitrophenyl)-3,5-pyridinedicarboxylate, and decarboxylating the diacid. 3-Methyl-4-(m-nitrophenyl)pyridine was prepared by replacing I with 2-propionylfuran in the first synthesis.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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 A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine, published in 2011-12-02, which mentions a compound: 6797-13-3, Name is 2-Ethylbenzo[d]oxazole, Molecular C9H9NO, Application In Synthesis of 2-Ethylbenzo[d]oxazole.

A divergent and regioselective synthesis of either 3-substituted benzoisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzoisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, resp. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Reference of 2-Mercapto-5-methylbenzimidazole. 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: 2-Mercapto-5-methylbenzimidazole, is researched, Molecular C8H8N2S, CAS is 27231-36-3, about Comparative toxicokinetic study of rubber antioxidants, 2-mercaptobenzimidazole and 2-mercaptomethylbenzimidazole, by single oral administration in rats. Author is Sakemi, kazue; Usami, Makoto; Mitsunaga, katsuyoshi; Ohno, Yasuo; Tsuda, Mitsuhiro.

Toxicokinetics of 2-mercaptobenzimidazole (MBI) and 2-mercaptomethylbenzimidazole (MMBI), rubber antioxidants with thioureylene structure, were compared after single oral administration in rats. Male Wistar rats received single oral administration of 2, 10, 50, and 250 mg/kg MBI or MMBI. The serum and urine concentrations of MBI and MMBI were determined by HPLC. MBI and MMBI showed similar Cmax values, but the former disappeared slower in the serum than the latter and resulted in its larger AUC values. Analyses of MBI, MMBI, and their desulfurated metabolites in urine suggested that these differences were due to their metabolic elimination rates. On the other hand, MBI and MMBI caused similar acute toxicities, such as the loss of locomotive activity, ataxic gait, adoption of prone or side position, and coma, being severer with higher serum concentrations at the moment. Similar acute toxicities between MBI and MMBI were explained by similar Cmax values at the same dose. It was suggested from these results that the slower disappearance and larger AUC values of MBI in the serum compared to MMBI might explain the strong thyroid toxicity which has been observed by repeated administration of MBI, but very weak thyroid toxicity by MMBI.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

HPLC of Formula: 6797-13-3. 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: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Aldol-type reaction of 2-ethylbenzazoles with aromatic aldehydes in aqueous medium.

The benzoxazole I (X = O) reacted with R1C6H4CHO (R1 = H, 2-Cl, 4-Cl, 2-Me, 4-Me, 4-MeO) in the presence of PhCH2N+Et3Cl- to give II (X = O) as erythro-threo mixtures, except for II (X = O, R1 = 4-MeO) which was pure erythro isomer. Similar reaction of I (X = S) with R1C6H4CHO (R1 = H, 4-Cl, 4-Me, 4-MeO) for 2 h gave II (X = S), whereas after 24 h III were obtained.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Pizzetti, Marianna; De Luca, Elisa; Petricci, Elena; Porcheddu, Andrea; Taddei, Maurizio published an article about the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1 ).Reference of 2-Ethylbenzo[d]oxazole. 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:6797-13-3) through the article.

The synthesis of benzimidazoles starting from o-phenylenediamines and amines in the presence of palladium on charcoal as catalyst is reported. Under microwave dielec. heating it is possible to use a tertiary, a secondary, and even a primary amine as the substrate for a palladium-mediated process to get 2-substituted or 1,2-disubstituted benzimidazoles, depending on the nature of the o-phenylenediamine employed. Primary amines are the most suitable reagents for the atom economy of the overall process. Benzoxazoles can be also prepared starting from primary amines and o-aminophenol. The reaction is also highly selective as no (poly)alkylated phenylenediamines or cross-contaminated benzimidazoles are obtained starting from N-monoalkylphenylenediamines. This behavior was interpreted as a scarce aptitude to dehydrogenation of the methylene bonded to the aromatic NH of N-alkylarylamines. The catalyst can be recycled several times and, although far from optimal, catalyst TON=90 is encouraging for further large-scale optimization protocols. In addition, the palladium on charcoal-catalyzed microwave-assisted reaction of o-phenylenediamine gives dealkylation of tertiary amines and transformation to the secondary amines.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Formula: C7H8O2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-(Furan-2-yl)propan-1-one, is researched, Molecular C7H8O2, CAS is 3194-15-8, about New Components with Potential Antioxidant and Organoleptic Properties, Detected for the First Time in Liquid Smoke Flavoring Preparations. Author is Guillen, Maria D.; Ibargoitia, Maria L..

A com. aqueous smoke preparation was exhaustively extracted, using dichloromethane as solvent, until the carrier had totally lost its smoky odor. Qual. and quant. characterizations of the extract were performed by means of gas chromatog./mass spectrometry and gas chromatog. with flame ionization detector, resp. Carbonyl derivatives including aldehydes and ketones as well as acids and esters are almost absent; however, the high proportion of phenol, guaiacol, and syringol derivatives is noticeable. The presence of di-tert-butylhydroxytoluene, several hopanes, and a number of lignin dimers must be pointed out; these latter components had apparently not been detected before either in smoke flavorings or in wood smoke. The mass spectral data of the compounds considered as lignin dimers and of the unidentified components are given. The presence of lignin dimers is very interesting from the point of view of health and food technol. for their therapeutic, organoleptic, and antioxidant properties.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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 Furan compounds. V. Preparation and configuration of furyl ketoximes, published in 1958, which mentions a compound: 3194-15-8, mainly applied to , Name: 1-(Furan-2-yl)propan-1-one.

cf. C.A. 45, 5676i. Several pairs of syn- and anti-furyl ketoximes were prepared, characterized, and their configuration established chem. and by UV absorption spectra determinations NaOH (100 g.) in 110 mL. H2O stirred with cooling with 86.9 g. HONH2.HCl in 220 mL. H2O and the mixture stirred 3 h. at 25-30° with 110 g. 2-furyl Me ketone, 2-RC4H3O (I) (R = Ac), the solution treated with 200 mL. saturated NH4Cl solution and the product washed with H2O yielded 80% anti-2-furyl Me ketoxime, anti-2-RC4H3O (II) (R = MeC:NOH) (IIa), m. 104°; HCl salt, m. 85-90°. IIa (10 g.) in 250 mL. Et2O at 0° saturated with dry HCl until the initial precipitate redissolved and the solution kept overnight, evaporated in vacuo and the residue washed with 2N Na2CO3, filtered and the precipitate recrystallized (H2O) gave 6.5 g. syn-IIa, m. 74°; HCl salt, m. 128-9°. Syn-IIa (1 g.) in 10 mL. 2N H2SO4 at 80° kept overnight at room temperature, neutralized with 2N Na2CO3, and the product crystallized (alc.) gave 0.6 g. anti-IIa. Furan (102 g.) and 390.4 g. (EtCO)2O at 40° treated in 5 min. with 15 mL. 85% H3PO4 and the mixture stirred 1 h. at 60-5°, the cooled mixture neutralized with 600 mL. 50% KOH and extracted repeatedly with Et2O, the extract dried (Na2SO4) and evaporated yielded 72% I (R = EtCO) (Ia), b11 74-5°. NaOH (50 g.) in 150 mL. H2O stirred with cooling with 43.5 g. HONH2.HCl in 150 mL. H2O and the mixture treated dropwise with 62.1 g. Ia at 25-30°, the mixture stirred 3 h. and the solution treated with 120 mL. saturated NH4Cl solution, the solidified product filtered off and taken up in 180 mL. alc., the filtered solution chilled, and diluted with 400 mL. H2O gave 35 g. pure anti-II (R = EtC:NOH) (IIb), m. 73°. Working up the mother liquor yielded 23 g. impure anti-IIb, m. 48-50°. Conversion of anti-IIb through the HCl salt in Et2O and crystallization of the crude product (dilute alc.) yielded 83% authentic syn-IIb, m. 77-8°. HONH2.HCl (46 g.), 56.2 g. anhydrous NaOAc, and 94.6 g. I (R = Bz) refluxed 1 h. in 550 mL. absolute alc. and the solution filtered hot, the residue washed with 140 mL. absolute alc. and the filtrate and washings kept 2 days, filtered, and the product recrystallized (EtOAc) yielded 23% anti-II (R = PhC:NOH) (IIc), m. 161°. Concentration of the mother liquor and treatment of the isomeric mixture (72 g., m. 132-5°) with HCl in Et2O yielded 96% syn-IIc, m. 149° (dilute alc.). Ac2O (510 g.) and 205.3 g. α-methylfuran treated as above with 25 g. 85% H3PO4 yielded 38% 5-methyl-2-furyl Me ketone (III), b12 78-80°. III (115 g.) in 650 mL. alc. and 77.6 g. HONH2.HCl in 240 mL. H2O containing 95.4 g. anhydrous NaOAc kept 16 h. and evaporated in vacuo with passage of 400-50 mL. alc., the concentrate diluted with 1 l. H2O and the solution chilled, 1 h. filtered, and the crystalline product (117 g.) recrystallized (400 mL. C6H6 and 100 mL. C6H6) gave 66 g. pure anti-5-methyl-2-furyl Me ketoxime (anti-IV), m. 83°. Concentration of the 2 mother liquors and treatment with HCl in Et2O yielded 88% syn-IV, m. 109°. HONH2.HCl (69.5 g.) in 120 mL. H2O and 100 g. NaOH in 120 mL. H2O added to a hot solution of 111 g. 2-benzofuryl Ph ketone (V) (cf. Stoermer, et al., C.A. 18, 2160) in 2 l. MeOH and the mixture boiled 20 min., concentrated and the residue treated with 750 mL. H2O and 250 mL. saturated NH4Cl solution, the precipitate taken up in a min. of alc., and the filtered solution diluted with H2O gave 111 g. isomeric mixture of anti- and syn-2-benzofuryl Ph ketoxime (anti-VI and syn-VI) (VII). VII (53.4 g.) shaken with 267 mL. Ac2O and the solution kept 1 day, filtered from 10.6 g. anti-VI acetate (VIa), m. 146°, and the filtrate diluted with 2 volumes ice H2O, neutralized with solid Na2CO3, and the solid product (50 g.) recrystallized (alc. and EtOAc) gave 18.9 g. VIa. VIa (20 g.) heated in 200 mL. 2N NaOH and the cooled solution diluted with 200 mL. H2O, stirred with 85 mL. saturated NH4Cl solution and filtered, the precipitate washed with H2O and dried in vacuo, taken up in a min. of warm PhMe and the filtered solution treated with petr. ether, the crude oxime (11.7 g., m. 140-53°) taken up in hot alc., and the solution diluted with H2O gave 10 g. anti-VI, m. 156°. Rearrangement of VII or pure anti-VI with HCl in Et2O gave syn-VI, m. 145° (dilute MeOH). anti-2-Benzofuryl Me ketoxime (anti-VIII), m. 154-5° (cf. C.A. 44, 2973d), rearranged yielded 84% syn-VIII, m. 161°. The oximes shaken with 10 volumes Ac2O and the solutions kept 3 h., poured into ice H2O, and neutralized with Na2CO3 gave the acetates. The oximes (0.01 mol) in 10 mL. C5H5N acetylated with equivalent amounts of BzCl or p-MeC6H4SO2Cl at -5 to -10°, kept 1 h. at 0° and poured into ice H2O, filtered, and the precipitate washed with H2O and dried over H2SO4 and KOH gave the benzoates and tolylsulfonates [oxime, and m.p. (solvent of crystallization) of acetate, benzoate, and tolylsulfonate given]: syn-IIa, 75° (H2O), 84° (petr. ether), 88° (C6H6-petr. ether); anti-IIb, 94° (petr. ether), 93° (petr. ether), 68°; anti-IIc, 109-10° (petr. ether), 144° (EtOAc), 84° (Me2CO-H2O); syn-IIc, 68° (petr. ether), 99-100° (alc.), 118°; anti-IV, 66° (petr. ether), 86° (petr. ether), 72° (decomposition) (C6H6-petr. ether); syn-IV, 94° (petr. ether), 95° (petr. ether), 112°; anti-VIII, 95-6° (petr. ether), 135-6° (alc.), 100-2°; syn-VIII, 77° (petr. ether), 90° (petr. ether), 140° (Me2COH2O); anti-VI, 146°, 152° (alc.), 116-18° (C6H6-petr. ether); syn-VI, 81° (alc.), 120° (alc.), 112° (C6H6-petr. ether). Anti-VI (10.2 g.) in 20 mL. C5H5N treated gradually at -5 to -10° with 9 g. r-MeC6H4SO2Cl and the mixture kept 1 h. at 0°, poured into 150 mL. ice H2O and the oily product triturated with Me2CO, the trituration diluted with H2O and filtered, and the precipitate washed with 2N HCl and H2O gave 15.25 g. anti-VI p-toluenesulfonate, m. 116-18° (Me2CO-ice H2O and C6H6-petr. ether). The preparation of the pairs of ketoximes permitted for the 1st time a systematic comparative spectroscopic examination UV absorption spectra for furfural oxime (IX), IIa, IIb, and IV showed a single maximum at 270 mμ, IIc had 2 maximum, and the spectra of VI and VIII were complicated. The syn- and anti-isomers showed a small difference in wave length but a larger difference in intensity. Based on the established configuration of IX, the chem. assigned configurations were spectroscopically confirmed. The preferential formation of anti-isomers in alk. media and of isomeric mixtures in neutral or acid media and the mechanism of the rearrangement in ethereal HCl were discussed.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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 Characterization of volatile compounds in three commercial Chinese vinegars by SPME-GC-MS and GC-O, published in 2019-09-30, which mentions a compound: 3194-15-8, mainly applied to vinegar volatile compound SPME GCMS GCO, Electric Literature of C7H8O2.

Headspace solid-phase microextraction (HS-SPME) coupled with gas chromatog.-mass spectrometry (GC-MS) and gas chromatog.-olfactometry (GC-O) were carried out to qual. and quant. characterize the volatiles and aroma-active compounds in three com. Chinese vinegars, including Zhengrong Rice Vinegar (ZRV), Zhenjiang Aromatic Vinegar (ZAV), and Longmen Smoked Vinegar (LSV). With the aid of DVB/CAR/PDMS fiber, a total of 75 volatile compounds were identified. Among them, 42 aromas were confirmed by their corresponding authentic chems. After comparison of the identified volatiles between the three vinegars, the ZAV sample was found to contain more alcs. and acids, the ZRV sample had more esters and phenols, while the LSV sample was shown to have more identified compounds in the ketones, aldehydes, and pyrazines. In regard to the quantitation, the volatiles that were found in high concentrations included acetic acid (at 14.64, 31.95 and 194 mg/L), furfural (at 5.49, 43.81 and 33.01 mg/L) and tetra-Me pyrazine (at 10.39, 13.51 and 19.41 mg/L) in ZRV, ZAV and LSV, resp. Moreover, thirty volatiles were identified by GC-O as aroma-active compounds that made contributions to the resp. flavor profiles of the com. Chinese vinegar. Eighteen of them were recognized as contributors for all the three com. Chinese vinegars under this study.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – 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 Studies on proton pump inhibitors. I. Synthesis of 8-[(2-benzimidazolyl)sulfinyl]-5,6,7,8-tetrahydroquinolines and related compounds, published in 1989-06-30, which mentions a compound: 27231-36-3, mainly applied to benzimidazolylsulfinyltetrahydroquinoline preparation antisecretory antiulcer; structure activity benzimidazolylsulfinyltetrahydroquinoline, Related Products of 27231-36-3.

Many 8-[(2-benzimidazolyl)sulfinyl]-5,6,7,8-tetrahydroquinolines were synthesized and examined for their (H+ + K+) ATPase ATPase-inhibitory and antisecretory activities. These sulfinyl compounds could be considered to be rigid analogs of the 2-[(2-pyridyl)methylsulfinyl]benzimidazole class of antisecretory agents. All the compounds tested were potent inhibitors of (H+ + K+)ATPase. Most of the compounds also inhibited histamine-induced gastric acid secretion in rats. Among them, 8-[(5-fluoro-2-benzimidazolyl)sulfinyl]-3-methyl-5,6,7,8-tetrahydroquinoline (I) was found to have the most potent activity. The structure-activity relationships are discussed.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem