Tag: M.W:100-200

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 of 3-pyridinols. III. Synthesis of pyridoxine skeletons from 4-methyloxazole, published in 1965, which mentions a compound: 148-51-6, Name is 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, Molecular C8H12ClNO2, Application In Synthesis of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride.

Pyridoxine dimethyl ether (I) and 4-deoxypyridoxine (II) were synthesized from 4-methyloxazole (III). 3-Cyano-5-hydroxy-6-methylpyridine (IV) was converted via the 4-CN derivative (V) to pyridoxine by the method of Okamoto and Tani (CA 54, 22644d). (MeOCH2CHBr)2 (5.5 g.) refluxed 1 hr. with 1.23 g. KOH in 12 cc. MeOH gave 2.2 g. MeOCH2CBr:CHCH2OMe (VI), b12 75-8°. VI (5.5 g.) and 3.5 g. CuCN heated 7 hrs. at 150° in an autoclave yielded 2.9 g. MeOCH2CH:C(CN)CH2OMe (VII), b8 84-6°. III (0.8 g.), 2.1 g. VII, 0.2 cc. H2O, and 4 cc. AcOH heated 40 hrs. at 95°, and the crude product chromatographed on Al2O3 yielded 2-methyl-4,5-bis(methoxymethyl)-3-pyridinol-HCl (VIII.HCl), m. 143-4° (iso-PrOH); picrate m. 168°. III (0.80 g.), 2.3 g. MeCH:CHCO2Et, 0.18 cc. H2O, and 3 cc. AcOH heated 20 hrs. at 90° in a sealed tube gave 0.2 g. (crude) Et 5-hydroxy-4,6-dimethylnicotinate, m. 146-8° (Me2CO). VIII (80 mg.) in 15 cc. dry tetrahydrofuran treated 72 hrs. at room temperature with 50 mg. LiAlH4 in 15 cc. dry tetrahydrofuran, and the filtered mixture acidified to pH 2 with dilute HCl and evaporated gave II.HCl, m. 255-7° (decomposition) (EtOH). IV (4.0 g.) in 90 cc. AcOH heated 1 hr. at 100° with 6 cc. 30% H2O2, treated twice with addnl. 6 cc. 30% H2O2 each time 1 and 4 hrs. gave 3.3 g. 5hydroxy-6-methylnicotinonitrile 1-oxide (IX), m. 278-80° (decomposition). IX (0.7 g.) and 0.7 g. Et2SO4 heated 2 hrs. at 100-10° gave 0.31 g. 1-ethoxy-2-methyl-3-hydroxy-5-cyanopyridinium ethosulfate, m. 129-30°. IX (0.6 g.) and 0.55 g. Me2SO4 heated 2 hrs. at 100-10°, and the resulting sirup added in 5 cc. H2O dropwise with shaking at 5-7° to 0.65 g. KCN in 8 cc. H2O and kept 1.5 hr. at room temperature gave 0.55 g. V, m. 189-90°.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Formula: C10H8ClN. 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: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins. Author is Denny, William A.; Atwell, Graham J.; Roberts, Peter B.; Anderson, Robert F.; Boyd, Maruta; Lock, Colin J. L.; Wilson, William R..

A series of isomeric 4-[[3-(dimethylamino)propyl]amino]nitroquinolines, e.g., I [Rn = H, 3-, 5-, 6-, 7-, 8-NO2, 2,5-Me(O2N), 3,5-Me(O2N), 6,5-Me(O2N), 8,5-Me(O2N), 7,8-Me(O2N), 7,6-Me(O2N), 2,3-Me(O2N)], has been synthesized and evaluated as hypoxia-selective cytotoxins and as radiosensitizers of hypoxic cells. The compounds showed widely-differing hypersensitivity factors (ratios of cytotoxicity against wild-type and repair-deficient mammalian cells). Many compounds showed oxygen-sensitive bioreduction resulting in DNA alkylation, while others show oxygen-insensitive modes of action. Of the nitro isomers studied, the 5-nitro showed the greatest hypoxic selectivity. A series of ring-substituted analogs were then prepared, in an effort to lower its reduction potential of -286 mV. Structure-activity studies showed that the effects of substitution on reduction potential were complex, being mediated by electronic and steric effects on the nitro group, as well as by effects on quinoline pKa. Two compounds of lower reduction potential, the 3- and 8-Me analogs, showed improved selectivity (47- and 60-fold in a clonogenic assay). These two compounds also showed the highest in vitro therapeutic indexes of the series as hypoxic cell radiosensitizers. Despite these favorable in vitro properties, neither compound had activity against hypoxic cells in SCCVII tumors when administered at 60% of the maximum tolerated dose.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of C5H11NO. 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: (S)-3-Methoxypyrrolidine, is researched, Molecular C5H11NO, CAS is 120099-61-8, about Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer-dimer interface. Author is Carney, Daniel W.; Lukesh, John C. III; Brody, Daniel M.; Brutsch, Manuela M.; Boger, Dale L..

Approaches to improving the biol. properties of natural products typically strive to modify their structures to identify the essential pharmacophore, or make functional group changes to improve biol. target affinity or functional activity, change phys. properties, enhance stability, or introduce conformational constraints. Aside from accessible semisynthetic modifications of existing functional groups, rarely does one consider using chem. synthesis to add mol. complexity to the natural product. In part, this may be attributed to the added challenge intrinsic in the synthesis of an even more complex compound Herein, we report synthetically derived, structurally more complex vinblastines inaccessible from the natural product itself that are a stunning 100-fold more active (IC50 values, 50-75 pM vs. 7 nM; HCT116), and that are now accessible because of advances in the total synthesis of the natural product. The newly discovered ultrapotent vinblastines, which may look highly unusual upon first inspection, bind tubulin with much higher affinity and likely further disrupt the tubulin head-to-tail α/β dimer-dimer interaction by virtue of the strategic placement of an added conformationally well-defined, rigid, and extended C20′ urea along the adjacent continuing protein-protein interface. In this case, the added mol. complexity was used to markedly enhance target binding and functional biol. activity (100-fold), and likely represents a general approach to improving the properties of other natural products targeting a protein-protein interaction.

Compounds in my other articles are similar to this one((S)-3-Methoxypyrrolidine)Electric Literature of C5H11NO, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 Nicotinamide inhibitors, published in 1952, which mentions a compound: 148-51-6, Name is 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, Molecular C8H12ClNO2, Name: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride.

3,5-Pyridinedicarboxylic acid, 2,3-pyrazinedicarboxylic acid, 4-methyl-2,3-pyridinedicarboxylic acid, 2,3-pyrazinedicarboxamide, 3-bromopyridine, 2-methyl-3-amino-4,5-bis(aminomethyl)pyridine, N-thiazolylpyrazinamide, N,N-dimethylpyrazinamide, N-methylpyrazinamide, N-pyrazinylthiourea, N-(hydroxymethyl)pyrazinamide, diethyl N-pyrazinoylaspartate, N-pyrazinoylpiperidine, N-isobutylpyrazinamide, N-(2-pyridyl)pyrazinamide, N-(3-pyridyl)pyrazinamide, N-phenylpyrazinamide, N-hexadecylpyrazinamide, 3-pyrazinoylaminoquinoline, N-(2-hydroxyethyl)-N’-pyrazinoylethylenediamine, 3-hydroxy-6-pyridazinecarboxamide, 2-pyrrolidone-5-carboxamide, 1-thiazolyl-2-pyrrolecarboxamide, desoxypyridoxine, salicylamide, furoic acid, furanilide, pyrazinohydrazide, 1-carbethoxy-4(1,2-dicarbethoxyethyl)piperazine, N-(p-methoxybenzyl)pyrazinamide, pyrazinohydroxamic acid, and Et N-pyrazinoyl-β-alanate had no anti-nicotinamide activity when tested against Lactobacillus arabinosus and none stimulated growth. Pyrazinamide, pyrazinoic acid, and 2-sulfanilamido-5-nitropyridine reversibly inhibited the action of nicotinamide on the organism. Pyrazinamide was not a nicotinamide antagonist for rats or chicks.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 2-ethylthioisonicotinamide》. Authors are Gustak, E.; Koruncev, D.; Gluncic, B..The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Related Products of 148-51-6. Through the article, more information about this compound (cas:148-51-6) is conveyed.

2-Ethylisonicotinaldehyde diethylacetal (I), b14 125-8°, was prepared in 61% yield from EtBr 112.2, Mg 33, 2-ethyl-4-bromopyridine 62, tri-Et orthoformate 180, and NH4Cl 215 g. Hydrolysis of 15.3 g. I with 150 ml. 10% HCl gave 83% free aldehyde (II), b20 92-5°; hydrazone m. 46-8°; thiosemicarbazone m. 215-16°. Willgerodt reaction of 0.75 g. II with 0.16 g. S in 30 ml. pyridine and 20 ml. NH3 yielded 56.5% of 2-ethylthioisonicotinoylamide.

In some applications, this compound(148-51-6)Related Products of 148-51-6 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Recommanded Product: 18436-73-2. 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: 4-Chloro-8-methylquinoline, is researched, Molecular C10H8ClN, CAS is 18436-73-2, about Rapid Microwave-Assisted, Solvent-Free Approach to Functionalization of 8-Methylquinolines via Rh-Catalyzed C(sp3)-H Activation. Author is Zhu, You-Quan; He, Jing-Li; Niu, Yun-Xia; Han, Ting-Feng; Zhu, Kun.

A microwave-assisted synthesis of aryl (quinolinyl)acetamide derivatives I [R1 = H, 6-Cl, 4-Br, etc.; R2 = 3-Me, 4-F, 4-Cl, etc.] and quinolinyl (methyl)benzamide II via Rh-catalyzed C(sp3)-H activation of 8-methylquinoline under solvent-free condition was reported. In comparison with traditional method, this reaction proceeded more efficiently with excellent yield, a broad range substrate scope and good functional group tolerance.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Biological comparison of synthetic and natural adermin》. Authors are Moller, E. F.; Zima, O.; Jung, F.; Moll, Th..The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Recommanded Product: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. Through the article, more information about this compound (cas:148-51-6) is conveyed.

Synthetic adermin was assayed by its influence on growth and acid formation by Streptobact. plantarum (C. A. 32, 9165.1); curves of growth (turbidity) and acidity vs. time are given. The synthetic preparation is slightly more active than the vitamin preparation made from rice hulls. A growth effect upon Streptobact. plantarum is likewise exhibited by 2,4-dimethyl-3-hydroxy-5-(hydroxymethyl)pyridine (hydrochloride m. 254°) although in 50-fold dose the result was only 30-40% of that of the B6 hydrochloride. The 4-desoxyadermin in single doses of 1000 γ is inactive on dermatitic rats.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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, U.S. Gov’t, P.H.S., Epilepsia called Effects of alterations in the metabolism of γ-aminobutyrate on convulsant potencies, Author is Stone, William E., which mentions a compound: 148-51-6, SMILESS is OC1=C(C)C(CO)=CN=C1C.[H]Cl, Molecular C8H12ClNO2, Formula: C8H12ClNO2.

Drugs that alter γ-aminobutyrate (GABA) [56-12-2] metabolism and presumably affect the availability of GABA in synaptic regions were tested for their relative effects on the potencies of 4 convulsants: 3-mercaptopropionate (3-MP) [107-96-0], pentamethylenetetrazole (PTZ) [54-95-5], bicuculline [485-49-4], and picrotoxin [124-87-8] in mice. Aminooxyacetic acid hemichloride [2921-14-4] given prior to the convulsant tended to decrease the potency of 3-MP more than that of PTZ. It decreased the potency of bicuculline more than that of PTZ but less than that of 3-MP, and did not alter that of picrotoxin. Thiocarbohydrazide (TCH) [2231-57-4], DL-C-allylglycine [7685-44-1], and 4-deoxypyridoxine-HCl (DOP) [148-51-6] tended to potentiate 3-MP more than PTZ. The effects of allylglycine on bicuculline and picrotoxin were intermediate. DOP potentiated bicuculline and picrotoxin only to the extent that it potentiated PTZ. TCH resembled DOP in its effect on bicuculline. Valproic acid [99-66-1] decreased the potency of each convulsant; it was most effective against PTZ, slightly less so against 3-MP, and still less effective against bicuculline and picrotoxin. Its anticonvulsive action probably is not primarily via the GABA system. Phenelzine [51-71-8] slightly decreased the potency of bicuculline, but potentiated 3-MP and picrotoxin and did not affect the potency of PTZ. Diacetyl monoxime [57-71-6] was anticonvulsive against PTZ, bicuculline, and picrotoxin, but not against 3-MP. The results do not support the view that bicuculline and picrotoxin induce seizures by blocking GABA-mediated inhibition.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Gurunadham, G.; Madhusudhan, Raju R. published the article 《New and alternate synthesis of lacosamide with chemoenzymatic method》. Keywords: enzymic resolution racemic lacosamide; lacosamide enantiopure preparation.They researched the compound: 2-Bromo-3-methoxypropanoic acid( cas:65090-78-0 ).Formula: C4H7BrO3. 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:65090-78-0) here.

Lacosamide [(R)-2-acetamido-N-benzyl-3-methoxy propionamide] 5 is a novel antiepileptic drug. Lacosamide was prepared by a chem. method with enzymic resolution of racemic lacosamide. Herein is reported an expedient four-steps enantioselective synthesis of lacosamide 5 beginning with Me 2,3-dibromo propionate 1. A new resolution process catalyzed by Novozyme 435. The products were obtained in very good yields and in a state of high purity. All the newly synthesized compounds (2-5) were characterized by their spectral (IR, 1H NMR, C13 NMR and MS) data.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Computed Properties of C8H12ClNO2. 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: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, is researched, Molecular C8H12ClNO2, CAS is 148-51-6, about Amino derivatives of pyridoxine and its analogs. Author is Yakovleva, N. L.; Balyakina, M. V.; Gunar, V. I..

Treatment of pyridines I (R = OH, R1 = Me, R2 = CH2OH (II); RR1 = OCMe2CH2O, R2 = CH2OH; R = OH, R1 = CH2OH, R2 = Me) with OP(NMe2)3 gave III (R = OH, R1 = Me, R2 = CH2NMe2 (IV); R = OH, R1 = CH2OH, R2 = CH2NMe2; R = OH, R1 = CH2 NMe2, R2 = Me). Heating II with SOCl2 gave I (R = OH, R1 = Me, R2 = CH2Cl), which was transformed to IV by reaction with Me2NH. Reaction of I (R3 = Cl) with HNMe2 gave I (R3 = NMe2).

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia