Tag: M.W:100-200

Application In Synthesis of 1-Piperidineacetic 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: 1-Piperidineacetic Acid, is researched, Molecular C7H13NO2, CAS is 3235-67-4, about Glyoxal derivatives. III. Reaction of glyoxal with some secondary amines. Author is Kliegman, Jonathan M.; Barnes, Robert K..

Both 40 and 80% aqueous glyoxal reacted with morpholine in the cold to give 1,1,2,2-tetramorpholinoethane (I) which on vacuum distillation gave 1,1,2-trimorpholinoethane (II), but on boiling the reactions mixture gave 4-(morpholinoacetyl)morpholine (III). III was also obtained by treating II with moist Me2CHOH. I reacted with hydroxy aliphatics to give 1,2-dialkoxy-1,2-dimorpholinoethanes. Piperidine similarly gave piperidinoacetyl-piperidine. PhNHMe reacted with glyoxal to give 1-methyl-3-(N-methyl-N-phenylamino)indole.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Quality Control of 3,5-Dimethyl-4-nitropyridine 1-oxide. 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: 3,5-Dimethyl-4-nitropyridine 1-oxide, is researched, Molecular C7H8N2O3, CAS is 14248-66-9, about N-Oxides of 11-deficient N-heteroaromatics. VIII. Photochemical rearrangement of pyridine and quinoline 1-oxides having sterically hindered 4-nitro group. Author is Kaneko, Chikara; Yokoe, Ichiro; Yamada, Sachiko.

EtOH (550 ml.) containing 1 g. 3,5,4-Me2(O2N)C5H2NO irradiated (N atm.) 1.5 hrs. by a Hanovia 450 w. high-pressure Hg-arc lamp placed inside a watercooled pyrex immersion well, the solvent evaporated, and the residue recrystallized from 1:10 MeOH-Me2CO yielded 30% 3,5,4-Me2(HO)C5H2NO, m. 184°, (Hertog and Combe, CA 47, 5938c). A mechanistic pathway involving nitro-nitrite rearrangement as a key step was tentatively suggested. Steric hindrance by the 2 ortho Me groups may prevent abstraction of H from the solvents by the excited species and thus inhibit formation of the 4-hydroxyamino compound Under the above conditions photolysis of 4-nitroquinoline 1-oxide gave only 7% 2,4-dihydroxyquinoline, m. 300°, whereas 3-methyl-4-nitroquinoline 1-oxide gave 30% 3-methyl-2,4-dihydroxyquinoline, m. 264-5°; monoacetate, m. 241-3°. Contrary to the photolysis of 4-nitro derivatives of pyridine, 2-picoline, 3-picoline, and 2,6-lutidine 1-oxides, the presence of O did not affect the formative of these products but the yields of the corresponding 4-hydroxy derivatives were somewhat lower.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Synthetic Route of C7H13NO2. 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: 1-Piperidineacetic Acid, is researched, Molecular C7H13NO2, CAS is 3235-67-4, about On the pKa, distribution into organic solvents, Km and Vmax of piperidine N-derivatives and the cleavage of their N-C linkage by liver enzyme system. Author is Kimura, Katsuhiko; Nagaoka, Masao; Agatsuma, Hitoshi; Ohgiya, Shozaburo.

Values of pKa, Km, and Vmax, and percentage of nondissocd. type, and distribution coefficient in organic solvents were measured for N-derivatives of piperidine; N-Me- [626-67-5], N-(2-hydroxyethyl)- [3040-44-6], N-carboxymethyl- [3235-67-4], and N-cinnamyl- [70552-70-4] piperidines, 3-methyl-4-piperidinobutan-2-one (I) [42327-99-1], 1-phenyl-3-piperidinopropan-1-one [73-63-2], and 1,3-diphenyl-4-piperidinobutan-2-one [70552-69-1], and correlation between these values and N-C cleavage of these derivatives is discussed. In general, derivatives having smaller pKa and Km values and those having a larger percentage of nondissocd. type distribution coefficient, and Vmax values had a greater tendency for cleavage.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The synthesis of esters of some amino acids having pharmacological importance. I. The synthesis of esters of piperidino carboxylic acids》. Authors are Matkovics, Bela; Foldeak, Sandor; Porszasz, Janos; Sipos, Gyorgy.The article about the compound:1-Piperidineacetic Acidcas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1).Reference of 1-Piperidineacetic Acid. Through the article, more information about this compound (cas:3235-67-4) is conveyed.

RCH2CO2R’ (I), RCH2CH2CO2R’ (II), BzOCH2CH2R (III), and AcOCHMeCH2R (IV) were prepared I were prepared by condensing ClCH2CO2R’ with a secondary amine, II by boiling ClCH2CH2CO2R’ with the amine, and III by the reaction of an amino alc. with BzCl. The following I were obtained (R, R’, b.p.°/mm., m.p. of picrate, m.p. of HCl salt, and m.p. of methiodide are given): piperidino, Me, 69°/5, 115°, 214°, 163-4°; piperidino, Et, 68°/1, 122°, 117-17.5°, 160-60.3°; piperidino, Bu, 100-1°/4, 85°, -, 178°; piperidino, PhCH2, 134-5°/1, 137°, 133°, 91-6°; morpholino, Me, 77°/2, 143°, 150.5°, 147.5°; morpholino, Et, 86-7°/4, 163°, 181°, 132-3°; morpholino, Bu, 105.5-106°/3, -, 127-9°, 95-6°; morpholino, PhCH2, 164-5°/5, 143°, 149°, -; pyrrolidino, Me, 72-3°/8, 104°, -, 153°; pyrrolidino, Et, 59-60°/2, 119.5°, 133-3.5°, -; pyrrolidino, Bu, 81-2°/3, 109.5°, -, -; pyrrolidino, PhCH2, 134-5°/1, 159-60°, 139-40°, 156°. The following II were prepared (data as above): piperidino, Me, 72°/2, 164°, 189°, 147-8°; piperidino, Et, 102-3°/5, 131.5°, 169°, -; piperidino, Bu, 124-5°/6, 108-9°, 164.7°, -; piperidino, PhCH2, 149-50°/1, 113°, 193.5°, -; piperidino, Ph, 114-20°/3, -, 192-5°, -; piperidino, CPh3, 171°/1, -, 214°, -; morpholino, Me, 82°/2, 129°, 203°, 151°; morpholino, Et, 108°/6, 108°, 188-9°, -; morpholino, Bu, 131-2°/6, 150°, 173°, 115°; morpholino, PhCH2, 154°/1, 125°, 189-90°, -; pyrrolidino, Me, 76°/5, 147°, 128°, 166°; pyrrolidino, Et, 85°/6, 114°, 146°, -; pyrrolidino, Bu, 106-8°/5, 97°, 74-5°, 115°; pyrrolidino, PhCH2, 145-6°/3, 102°, 152°, 154°. IV (R =pyrrolidino) (V), b3 75°, picrate m. 111-12°, gave a hygroscopic HCl salt. III (R = piperidino) b2 141°; HCl salt m. 184°; methiodide m. 141.5°. The action of the compounds on blood pressure and on respiration was given. II (R = N-piperidino, R’ = CPh3) and V had strong antinicotinic action. The effect of the piperidino and pyrrolidino propionates was increased by quaternization.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Sojka, Stanley A.; Dinan, Frank J.; Kolarczyk, Robert published an article about the compound: 2-Chloropyridine 1-oxide( cas:2402-95-1,SMILESS:ClC1=CC=CC=[N+]1[O-] ).Category: isoxazole. 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:2402-95-1) through the article.

13C NMR spectra of substituted pyridine N-oxides were examined and compared to the spectra of the corresponding free pyridine bases. The N-oxide functionality causes significant shielding at the C-2, C-4, and C-6 positions. This shielding was associated with electron d. donation by the N-oxide functionality to these positions. The N-oxide functionality also caused an enhancement of the substituent α-effect for -NMe2, -OMe, and -NO2 groups.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – 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 Aqueous biphasic oxidation: a water-soluble polyoxometalate catalyst for selective oxidation of various functional groups with hydrogen peroxide, published in 2004-02-29, which mentions a compound: 2402-95-1, Name is 2-Chloropyridine 1-oxide, Molecular C5H4ClNO, Recommanded Product: 2-Chloropyridine 1-oxide.

A “”sandwich”” type polyoxometalate, Na12[WZn3(H2O)2][(ZnW9O34)2], was used as an oxidation catalyst in aqueous biphasic reaction media to effect oxidation of alcs., diols, pyridine derivatives, amines and aniline derivatives with hydrogen peroxide. The catalyst was shown by 183W NMR to be stable in aqueous solutions in the presence of H2O2 and showed only minimal non-productive decomposition of the oxidant. Secondary alcs. were selectively oxidized to ketones, while primary alcs. tended to be oxidized to the corresponding carboxylic acids, although secondary alcs. were selectively oxidized in the presence of primary alcs. Vicinal diols yielded carbon-carbon bond cleavage products in very high yields. Pyridine derivatives were oxidized to the resp. N-oxides, but strongly electron-withdrawing moieties inhibited the oxidation reaction. Primary amines were oxidized to the oximes, but significantly hydrolyzed in situ. Aniline derivatives were oxidized to the corresponding azoxy or nitro products depending on the substitution pattern in the aromatic ring. Catalyst recovery and recycle was demonstrated.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Formula: C5H4ClNO. 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-Chloropyridine 1-oxide, is researched, Molecular C5H4ClNO, CAS is 2402-95-1, about Catalytic Ynamide Oxidation Strategy for the Preparation of α-Functionalized Amides.

A Lewis acid-catalyzed alkyne oxidation strategy has been developed to produce diverse α-functionalized amides from readily and generally available ynamides. An efficient zinc(II)-catalyzed oxidative azidation and thiocyanation has been achieved, providing facile access to synthetically useful α-azido amides and α-thiocyanate amides, resp. This chem. can also be extended to oxidative halogenations by employing the 2-halopyridine N-oxide as both the oxidant and the halogen source, and its mechanistic rationale is also supported by d. functional theory calculations Moreover, NaBARF has been demonstrated to catalyze such an alkyne oxidation effectively, thus further excluding the metal carbene pathway in this cascade reaction.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – 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 Search for anticholinergic compounds. XLV. Structure and pharmacological activity of some esters of alkylamino acids: piperidino-, morpholino-, dicyclohexylamino-, phenylcyclohexylamino-, diphenylamino-, benzylphenylamino-, and benzylcyclohexylaminoacetic acids, published in 1985, which mentions a compound: 3235-67-4, Name is 1-Piperidineacetic Acid, Molecular C7H13NO2, Product Details of 3235-67-4.

The anticholinergic activity of a number of esters of acetic and aminoacetic acid derivatives was assessed as a function of the Schild index value. The highest activity was observed when piperidine was part of the alc. moiety and the acid moiety contained a branched substituent. With branched substituents in both the acid and the alc. moiety, activity decreased markedly. Aminoacetate esters were more active than the analogous acetate esters, the presence of 2 -O-C-C-N- groups in the mol. apparently being the reason behind this observation. 2-(1-Piperidinyl)ethyl diphenylaminoacetate  [102964-41-0] was more active than pipethanate  [4546-39-8].

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Amino acids. I. Synthesis of some tertiary aminoacetic acids》. Authors are Remizov, A. L..The article about the compound:1-Piperidineacetic Acidcas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1).Name: 1-Piperidineacetic Acid. Through the article, more information about this compound (cas:3235-67-4) is conveyed.

It was shown that reaction of ClCH2CO2H with R2NH depends on the basicity of the amine used and on steric factors. Benzylidenecyclohexylamine and MeI gave C6H11NHMe.HCl, m. 178-9°; free amine b62 73°. MeOCH2CH2Cl in MeOH-NH3 in 12 hrs. at 90-5° gave 5% MeOCH2CH2NH2, b. 92-5° (picrate m. 147-9°), 42% (MeOCH2CH2)2NH, b21 67-8°, n20D 1.4211 (picrate m. 112-14°; picrolonate m. 178-9°), and 19% (MeOCH2CH2)3N, b10 100-1°, 1.4330 (picrate m. 65-6°; picrolonate m. 119-20°). Shaking 0.06 mole ClCH2CO2H after neutralization with a paste of BaCO3 with 0.06 mole desired amine in H2O 4 hrs. followed by 20 hrs. at room temperature gave, after final heating on a steam bath to complete the reaction, RR’NCH2CO2H (NRR’ and m.p. given): Me2N, 179-81° (HCl salt m. 190-1°); Et2N, 135-6° (HCl salt m. 126-7°); piperidino, 208-11° (HCl salt m. 217-21°); morpholino, 162-3.5° (HCl salt m. 169-71°); C6H11NMe, 186-7° (HCl salt m. 166-7°); (MeOCH2CH2)2N, 48-9.5° (picrolonate m. 116-17°). These were accompanied by 2-20% RR’N(CH2CO2H)2Cl (same data given): NMe2, decomposed 208-9°; NEt2, decomposed 244-6°; MeNC6H11, decomposed 205-7°. For avoidance of formation of these salts, the secondary amines should be used in excess; alternatively, ClCH2CO2H was neutralized with aqueous NaOH and kept overnight with RR”NH, then heated on a steam bath.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Saleh, Maysaa M.; Laughton, Charles A.; Bradshaw, Tracey D.; Moody, Christopher J. published an article about the compound: 1-Piperidineacetic Acid( cas:3235-67-4,SMILESS:OC(=O)CN1CCCCC1 ).Reference of 1-Piperidineacetic Acid. 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:3235-67-4) through the article.

Maintenance of telomeres – specialized complexes that protect the ends of chromosomes – is provided by the enzyme complex telomerase, which is a key factor that is activated in more than 80% of cancer cells, but absent in most normal cells. Targeting telomere maintenance mechanisms could potentially halt tumor growth across a broad spectrum of cancer types. Telomeric ends of chromosomes consist of noncoding repeat sequences of guanine-rich DNA. These G-rich ends can fold into structures called G-quadruplexes. Stabilization of G-quadruplexes by small binding mols. called G4 ligands can prevent telomerase enzyme from maintaining telomere integrity in cancer cells. G-quadruplexes can exist in other parts of the genome too, especially within promoter sequences of oncogenes, and also be interesting drug targets. Here, we describe the development of a new series of novel bis-triazoles, designed to stabilize G-quadruplex structures selectively as G4 ligands. FRET assays showed two compounds to be moderately effective G4 binders, with particular affinity for the quadruplex formed by the Hsp90a promoter sequence, and good selectivity for G-quadruplex DNA vs. duplex DNA. However, CD spectroscopy failed to provide any information about the folding topol. of the human telomeric G-quadruplex resulting from its interaction with one of the ligands. All the new ligands showed potent cell growth inhibitory properties against human colon and pancreatic cancer cell lines, as evidenced by the MTT assay; notably, they were more potent against cancer cells than in fetal lung fibroblasts. Docking studies were performed to rationalize the affinity of these ligands for binding to the telomeric parallel G-quadruplex DNA.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem