Tag: M.W:100-200

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 Reaction of oxide radical ion (O·-) with substituted pyrimidines, published in 2002-06-30, which mentions a compound: 1194-22-5, mainly applied to reaction oxide radical substituted pyrimidine oxidizing radical electron transfer; pulse radiolysis reaction oxide radical substituted pyrimidine, Formula: C5H6N2O2.

Pulse radiolysis technique has been used to investigate the reaction of oxide radical ion (O·-) with 4,6-dihydroxy-2-Me pyrimidine (DHMP), 2,4-dimethyl-6-hydroxy pyrimidine (DMHP), 5,6-di-Me uracil (DMU) and 6-Me uracil (MU) in strongly alk. medium. The second-order rate constants for the reaction of O·- with these compounds are in the range 2-5 × 108 dm3 mol-1 s-1. The transient absorption spectra obtained with DHMP have two maxima at 290 and 370 nm and with DMHP have maxima at 310 and 470 nm. The transient spectrum from DMU is characterized by its absorption maxima at 310 and 520 nm and that of MU by its single maximum at 425 nm. The intermediate species were found to react with N,N,N’,N’-tetramethyl-p-phenylenediamine (TMPD) with high G(TMPD·+) values ranged between 3.9 × 10-7 mol J-1 and 4.8 × 10-7 mol J-1. These radicals undergo decay by second-order kinetics (2k/ε = 1.0-1.7 × 106 s-1). The reaction of O·- with the selected pyrimidines is proposed to proceed through a hydrogen abstraction from the Me group forming allyl type radicals. These are mainly oxidizing radicals and hence readily undergo electron transfer reactions with TMPD.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Infrared spectra of derivatives of pyrimidine》. Authors are Short, L. N.; Thompson, H. W..The article about the compound:6-Hydroxy-2-methylpyrimidin-4(3H)-onecas:1194-22-5,SMILESS:CC1=NC(=CC(N1)=O)O).Name: 6-Hydroxy-2-methylpyrimidin-4(3H)-one. Through the article, more information about this compound (cas:1194-22-5) is conveyed.

Graphs of the vibrational spectra between 2 and 25 μ are given for the following compounds suspended as solids in paraffin or perfluorokerosine, and for the deuterio derivatives of the starred compounds (deuteriated by treatment with D2O): pyrimidine, monosubstituted pyrimidines: 2-Cl-, 2-NH*2-, 5-NH2-2-OH-*, 4-OH-*, 2-SH-*; 2,4-disubstituted pyrimidines: Cl2-, (OEt)2, (OPh)2, 2-Cl-4-NH2-*, (OH)2-*, 2-OH-4-NH2-*, (NH2)2-(SH)2-*, 2-SH-4-NH2-, 2(-)SH-4-OH-*; 4,6-disubstituted pyrimidines: 4-NH2-6-Cl-*, 4-OH-6-Me-, (OH)2-, 4-OH-6NH2-*, (NH2)2-*, 2,4,6-trisubstituted pyrimidines: Cl3-, 2-Me-4,6-Cl2-, 2-NH2-4,6-Me*2-2-NH2-4,6-(OMe)2-, 2-NH2-4,6-Cl2-, 2-NH2-4-Me-6-OEt-*, 2-NH2-4-Me-6-Cl-*, 2,6-Cl2-4-NH2-, 2-Cl-4-NH2-6-Me-, 2,6-Me2-4-NH2-*, 2-Me-4-NH2-6-Cl-, 2-NHMe-4-Me-6-Cl-, 2,6-Me2-4-OH-, 2,4-(OH)2-6-Me-, 2-Me-4,6-(OH)2-, (OH)3-, 2-NH2-4-OH-6-Me-*, 2-NMe2-4-OH-6-Me-*, 2-NH2-4-OH-6-Cl-, 2-SMe-4-OH-6-NH2-, 2-Me-4-OH-6-NH2-*, (NH2)3-, 2,4-(OH)2-6-NH2-, 2-NH2-4,6-(OH)2-, 2,4-(NH2)2-6-OH, 2-OH-4,6-(NH2)2-, 2-SH-4-OH-6-Me-, 2-SH-4-OH-6-NH2-, 2-NH2-4-Me-6-CONH2-, 2-NH2-4-Me-6-CN-; also the 4-NH2-5-Ph-*, 2,4-(OH)2-5-NO2-, 4,6-(NH2)2-5-Br-, 2-Me-4,6-(OMe)2-5-NO2-, 2-Me-4,6-(OMe)2-5-NH2-, 2-SEt-4-OH-5-Et-6-Me-, 1,4-Me2-2-SMe-6-O-, 1,3-Me2-2,4-O2-, 2-NH2-3-Et-4-Me-6-O-, and 1-Et-2-NH2-4-Me-6-O- pyrimidine derivatives In the OH and NH2 pyrimidines with or without other substituents around the ring, the main regions connected with the possibility of tautomerism are at 6 μ and 3 μ. Since ambiguities occur in both these regions, exact frequency assignments are difficult to make. The spectra are highly characteristic with sharp bands and might be used for analysis and identification. The spectral evidence suggests a ketonic structure for simple 2-OH and 4-OH derivatives and probably a diketonic form for 2,4-(OH)2 derivatives In 4,6-dihydroxypyrimidine one CO and one OH group may be present. NH2-substituents are probably not tautomerized and have the character of an amido group. The electronic effects of different substituents may influence the tautomerism and the amount of H-bonding. These conclusions do not agree in some respects with those of Brownlie (C.A. 45, 2778d).

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Application of 1194-22-5. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 6-Hydroxy-2-methylpyrimidin-4(3H)-one, is researched, Molecular C5H6N2O2, CAS is 1194-22-5, about Influence of some derivatives and isomers of uracil, cytosine, and isocytosine on the growth of transplantable tumors. Author is Aksamitnaya, I. A..

5-Hydroxy-4-methyluracil, 4,5-dihydrouracil, 6-thiouracil, 6-thio-4-methyluracil, 2-methyl-4,6-dihydroxypyrimidine, or 4-amino-6-hydroxypyrimidine at 100-200 mg./ml. suppressed tumor growth by 9-32%, while 6-thiothymine and Na 4-methyl-5-sulfoisocytosine stimulated tumor growth by 33 and 41%, resp., in mice implanted with sarcoma 180 cells. 4-Amino-6-hydroxypyrimidine inhibited and Na 4-methyl-5-sulfoisocytosine stimulated growth of Ehrlich ascites tumors in mice. Thymine, 4-methyluracil, 4-methyl-4,5-dihydrouracil, 4-methylisocytosine, and 4-methyl-5-aminoisocytosine did not affect tumor growth in mice.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Reference of 6-Hydroxy-2-methylpyrimidin-4(3H)-one. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 6-Hydroxy-2-methylpyrimidin-4(3H)-one, is researched, Molecular C5H6N2O2, CAS is 1194-22-5, about On the Synthesis of 1,1-Diamino-2,2-dinitroethene (FOX-7) by Nitration of 4,6-Dihydroxy-2-methylpyrimidine. Author is Latypov, Nikolaj V.; Johansson, Martin; Holmgren, Erik; Sizova, Ekaterina V.; Sizov, Vladimir V.; Bellamy, Anthony J..

The synthesis of 1,1-diamino-2,2-dinitroethene (FOX-7) by nitration of 4,6-dihydroxy-2-methylpyrimidine and hydrolysis of the resulting intermediate 2-dinitromethylene-5,5-dinitropyrimidine-4,6-dione was studied. By varying the reaction parameters the optimal conditions for the synthesis of FOX-7 were identified and gave a >90% yield of the pure product. The optimized process allowed the spent acid to be recycled without loss of yield, with almost stoichiometric consumption of HNO3. The purity of the FOX-7 was determined by using a newly developed HPLC method.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

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.Fernandez-Saez, Nerea; Rubio-Ruiz, Belen; Campos, Joaquin M.; Unciti-Broceta, Asier; Carrion, Maria Dora; Camacho, Maria Encarnacion researched the compound: 2,6-Dichloropurine( cas:5451-40-1 ).Recommanded Product: 5451-40-1.They published the article 《Purine derivatives with heterocyclic moieties and related analogs as new antitumor agents》 about this compound( cas:5451-40-1 ) in Future Medicinal Chemistry. Keywords: breast colorectal cancer cell purine derivative antitumor; Mitsunobu; antiproliferative activity; apoptosis; benzoxazine; pyridoxazine; quinoline. We’ll tell you more about this compound (cas:5451-40-1).

Identification of new antiproliferative compounds Four series of compounds were synthesized by the Mitsunobu reaction. Their antiproliferative activity was studied against several cancer cells and a noncancerous fibroblast cell line. Their apoptotic activity was analyzed using a caspase 3/7 fluorescence assay. 9-Alkylated-6-halogenated and 2,6-dihalogenated purines show remarkable inhibition of tumor cell proliferation, with the dichloro derivatives being the most potent of all the series. The most promising compound, tetrahydroquinoline 4c, exhibits significant antiproliferative activity against the cancer cells tested, while displaying a 19-fold lower potency against noncancerous fibroblasts, a key feature that indicates potential selectivity against cancer cells. This compound produces a high percentage of apoptosis (58%) after 24 h treatment in human breast cancer MCF-7 cells.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Safety of Ethyl 3-bromo-2-oxopropanoate. 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: Ethyl 3-bromo-2-oxopropanoate, is researched, Molecular C5H7BrO3, CAS is 70-23-5, about Elastase inhibitor cyclotheonellazole A: Total synthesis and in vivo biological evaluation for acute lung injury. Author is Cui, Yingjun; Zhang, Mengyi; Xu, Honglei; Zhang, Tingrong; Zhang, Songming; Zhao, Xiuhe; Jiang, Peng; Li, Jing; Ye, Baijun; Sun, Yuanjun; Wang, Mukuo; Deng, Yangping; Meng, Qing; Liu, Yang; Fu, Qiang; Lin, Jianping; Wang, Liang; Chen, Yue.

Acute lung injury/acute respiratory distress syndrome (ALI/ARDS) is one of the most common complications in COVID-19. Elastase has been recognized as an important target to prevent ALI/ARDS in the patient of COVID-19. Cyclotheonellazole A (CTL-A) is a natural macrocyclic peptide reported to be a potent elastase inhibitor. Herein, we completed the first total synthesis of CTL-A in 24 linear steps. The key reactions include three-component MAC reactions and two late-stage oxidations We also provided seven CTL-A analogs and elucidated preliminary structure-activity relationships. The in vivo ALI mouse model further suggested that CTL-A alleviated acute lung injury with reductions in lung edema and pathol. deterioration, which is better than sivelestat, one approved elastase inhibitor. The activity of CTL-A against elastase, along with its cellular safety and well-established synthetic route, warrants further investigation of CTL-A as a candidate against COVID-19 pathogeneses.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 1194-22-5, is researched, Molecular C5H6N2O2, about Structure of 4,6-dihydroxypyrimidine derivatives studied by infrared spectra, the main research direction is pyrimidines hydroxy IR; IR hydroxypyrimidines.Quality Control of 6-Hydroxy-2-methylpyrimidin-4(3H)-one.

Ir spectra of 4,6-dihydroxypyrimidine derivatives were studied in the 1500-1800-cm.-1 region, in order to determine which tautomers are present in each case. Model compounds, with fixed structures were taken as references. 4,6-Dimethoxypyrimidine (I) has the fixed enol structure, and its ir bands at 1595 and 1555 cm.-1 correspond to ring vibrations. 1-Methyl-5-methoxy-6-pyrimidin-one (II) has both enol and keto forms fixed; it shows a strong band (1673 cm.-1 in Me2SO and 1660 cm.-1 in D2O) which is ascribed to the C:O stretching vibration. Weaker bands (1605 and 1550 cm.-1 in Me2SO, and 1603 and 1550 cm.-1 in D2O) are ascribed to the ring. 5,5-Diethyl-2-phenyl-4,6-pyrimidinedione (III), with partially fixed structure, can have 2 tautomeric forms. In Me2SO 2 C:O bands are seen at 1728 and 1682 cm.-1, and the diketo form is ascribed. IV, (R = Me), the structure of which was proven, has 2 carbonyls. One C:O band only can be expected, as for ionized carboxyl groups. Three bands are seen instead, in solution, and 2 of them should be ascribed to the ring vibrations. Potentially tautomeric compounds (14) were investigated in Me2SO and D2O solutions, and in the solid state. In Me2SO all the compounds have a strong C:O band at 1690-1660 cm.-1 and some other weaker bands, ascribed to ring and N-H bending frequencies, as for fixed enol and keto forms of II. The frequency of the C:O band depends on the nature of the substituent in position 5 on the ring; it is 1660 cm.-1 for 5-Me, 1658 for Ph, 1667 for H, 1672 for OPh, 1673 for Cl, 1673 for Br, and 1690 for NO2. The spectrum of 4,6-dihydroxypyrimidine (V), its mono-N-methyl-, 5-, and 2-methyl-substituted derivatives show 3 bands at 1675, 1648, and 1560 cm.-1 as does IV; the same type of spectra are given by the N-methyl-, 5-methyl-, and 2-methyl-substituted derivatives of V, showing that they exist in the bipolar form IV. The C:O band of the compounds in the solid state are wide and it is difficult to ascribe any form by comparing with the spectra of model compounds but the N-H bending frequencies are easy to ascribe, compared with the spectra of the corresponding deuterated compounds All the compounds may be divided in 2 groups: the 1st, with N-H bending frequencies of 1700-1640 cm.-1 includes V and its 2- and 5-methylsubstituted compounds; the 2nd with N-H bending frequencies of 1600-1560 cm.-1, as for 4-methoxy-6-hydroxypyrimidine, include compounds having electroneg. substituents such as Ph, Br, and NO2, in the 5 position of the ring. The higher N-H bending frequencies of the 1st group as compared with the frequency for the fixed structures II is explained by bipolar structure type IV. 5-Phenyl-, 5-bromo-, and 5-nitro-4,6-dihydroxypyrimidines exist in the keto and enol forms of II, or in the diketo form of III. The diketo form ascribed to 5-Br- and 5-NO2-substituted compounds is not final, because 2 bands could appear by splitting of the C:O band in II caused by intermol. interactions, in the crystals.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

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.Maki, Toshikatsu; Ishihara, Kazuaki; Yamamoto, Hisashi researched the compound: Pyridin-3-ylboronic acid hydrochloride( cas:265664-63-9 ).Synthetic Route of C5H7BClNO2.They published the article 《New boron(III)-catalyzed amide and ester condensation reactions》 about this compound( cas:265664-63-9 ) in Tetrahedron. Keywords: boron catalysis carboxylic acid esterification amidation green chem; polystyrene bound alkylated boronopyridinium salt preparation catalysis esterification amidation; Ritter addition catalysis benzodioxaborole; crystal structure cyclocondensed dodecamer quaternized boronopyridinium iodide; mol structure cyclocondensed dodecamer quaternized boronopyridinium iodide. We’ll tell you more about this compound (cas:265664-63-9).

In 1996, the authors reported that benzeneboronic acids bearing electron-withdrawing groups at the meta- or para-position are highly effective catalysts for the amide condensation reaction in less-polar solvents. The authors now report that N-alkyl-4-boronopyridinium halides are more effective catalysts than the previous ones in more polar solvents. N-Alkyl-4-boronopyridinium halides are effective not only for amide condensation between equimolar mixtures of carboxylic acids and amines but also for the esterification of α-hydroxycarboxylic acids in alc. solvents. Furthermore, perchlorocatecholborane is more effective than areneboronic acids for the amide condensation of sterically demanding carboxylic acids. Lewis acid-assisted Bronsted acid (LBA), which was prepared from a 1:2 M mixture of boric acid and tetrachlorocatechol, is effective for the Ritter reaction from alcs. and nitriles to amides. The crystal and mol. structures of a cyclocondensed dodecamer of 4-borono-1-methylpyridinium iodide were determined by x-ray crystallog.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

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, European Journal of Medicinal Chemistry called Purine/purine isoster based scaffolds as new derivatives of benzamide class of HDAC inhibitors, Author is Nepali, Kunal; Chang, Ting-Yu; Lai, Mei-Jung; Hsu, Kai-Cheng; Yen, Yun; Lin, Tony Eight; Lee, Sung-Bau; Liou, Jing-Ping, which mentions a compound: 5451-40-1, SMILESS is C2=NC1=C(C(=NC(=N1)Cl)Cl)[NH]2, Molecular C5H2Cl2N4, Product Details of 5451-40-1.

This study reports the design, synthesis and evaluation of a series of histone deacetylase (HDAC) inhibitors I (X = Cl, methylazanyl, (3-chloro-4-fluorophenyl)azanyl, etc.; Y = Cl, NH2, (2,4,6-trichloro-3,5-dimethoxyphenyl)azanyl; Z = N, CH; R = H, F) containing purine/purine isoster as a capping group and an N-(2-aminophenyl)-benzamide unit. In vitro cytotoxicity studies reveal that benzamide I (X = (3-chloro-4-fluorophenyl)azanyl; Y = NH2; Z = N; R = H) (A) suppressed the growth of triple-neg. breast cancer cells MDA-MB-231 (IC50 = 1.48μM), MDA-MB-468 (IC50 = 0.65μM), and liver cancer cells HepG2 (IC50 = 2.44μM), better than MS-275 and Chidamide. Compared to the well-known HDAC inhibitor SAHA, (A) showed a higher toxicity (IC50 = 0.33μM) in three leukemic cell lines, K-562, KG-1 and THP-1. Moreover, (A) was found to be equally virulent in the HDAC-sensitive and -resistant gastric cell lines, YCC11 and YCC3/7, resp., indicating the potential of (A) to overcome HDACi resistance. Furthermore, substantial inhibitory effects more pronounced than MS-275 and Chidamide were displayed by (A) towards HDAC1, 2 and 3 isoforms with IC50 values of 0.108, 0.585 and 0.563μM resp. Compound (A) also exhibited a potent antitumor efficacy in human MDA-MB-231 breast cancer xenograft mouse model, providing a potential lead for the development of anticancer agents.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

Bertrand, Jeanluc; Dostalova, Hana; Krystof, Vladimir; Jorda, Radek; Castro, Alejandro; Mella, Jaime; Espinosa-Bustos, Christian; Maria Zarate, Ana; Salas, Cristian O. published the article 《New 2,6,9-trisubstituted purine derivatives as Bcr-Abl and Btk inhibitors and as promising agents against leukemia》. Keywords: purine preparation SAR antileukemic activity cytotoxicity; Bcr-Abl inhibitors; Btk inhibitors; Docking; Leukemia; Purine derivatives; QSAR.They researched the compound: 2,6-Dichloropurine( cas:5451-40-1 ).Application In Synthesis of 2,6-Dichloropurine. 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:5451-40-1) here.

Bcr-Abl and Btk kinases are among the targets that have been considered for the treatment of leukemia. Therefore, several strategies have focused on the use of inhibitors as chemotherapeutic tools to treat these types of leukemia, such as imatinib (for Bcr-Abl) or ibrutinib (for Btk). However, the efficacy of these drugs has been reduced due to resistance mechanisms, which have motivated the development of new and more effective compounds In this study, 2,6,9-trisubstituted purine derivatives I (R = C6H5, 3-FC6H4, 4-CH3OC6H4, etc.; R1 = H, F) were designed, synthesized and evaluated as novel Bcr-Abl and Btk inhibitors. The compounds I (R = 3-FC6H4; R1 = H) and (R = 3,4-(F)2C6H3; R1 = H) were identified as potent inhibitors of both kinases (IC50 values of 40 nM and 0.58/0.66μM for Abl and Btk, resp.). From docking and QSAR analyses, it was concluded that fluorination of the arylpiperazine system is detrimental to the activity against two kinases, and also validated the hypothesis that the substitution on the 6-phenylamino ring is important for the inhibition of both kinases. In addition, the studies indicated that most compounds could suppress the proliferation of leukemia and lymphoma cells (HL60, MV4-11, CEM, K562 and Ramos cells) at low micromolar concentrations in vitro. Finally, the compound I (R = 3-FC6H4; R1 = H) inhibited the downstream signaling of both kinases in the resp. cell models. Therefore, I (R = 3-FC6H4; R1 = H) and (R = 3,4-(F)2C6H3; R1 = H) possessed potency to be further optimized as anti-leukemia drugs by simultaneously inhibiting the Bcr-Abl and Btk kinases.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem