Category: 7153-13-1

COA of Formula: C5H5Cl2N3. 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: 2-Amino-4,6-dichloro-5-methylpyrimidine, is researched, Molecular C5H5Cl2N3, CAS is 7153-13-1, about Synthesis and structure-activity relationship studies of polysubstituted pyrimidines as inhibitors of immune-activated nitric oxide production. Author is Jansa, Petr; Holy, Antonin; Dracinsky, Martin; Kolman, Viktor; Janeba, Zlatko; Kmonickova, Eva; Zidek, Zdenek.

Based on the previous discovery of the inhibitory effect of the 5-substituted 2-amino-4,6-dichloropyrimidines on nitric oxide (NO) production in vitro, a series of novel pyrimidine derivatives, namely 4,6-dichloro-2-[(N,N-dimethylamino)methyleneamino]pyrimidines, 2,4-diamino-6-chloropyrimidines, and 2,4-diamino-6-(2-hydroxyethoxy)pyrimidines, were prepared bearing various substituents at the C-5 position on the pyrimidine, such as hydrogen, Me, Et, Pr, iso-Pr, propargyl, allyl, Bu, sec-Bu, Ph, benzyl, and fluorine. The intrinsic biol. potential of the prepared compounds was characterized by effects on the in vitro production of immune-activated NO in mouse peritoneal cells. All 5-substituted 4,6-dichloro-2-[(N,N-dimethylamino)methyleneamino]pyrimidines strongly inhibited NO production The IC50s were <5 μM in most cases. The highest inhibitory activity was observed for the 5-s-Bu analog (IC50 = 2.57 μM), the lowest one for 5-unsubstituted compound (IC50 = 11.49 μM). With the exception of the 5-fluoro-4,6-dichloro-2-[(N,N-dimethylamino)methyleneamino] derivative, all other compounds were devoid of cytotoxic effects. The hitherto obtained data suggest that the NO-inhibitory activity depends on the presence of the 2-amino-4,6-dichloropyrimidine scaffold. 《Synthesis and structure-activity relationship studies of polysubstituted pyrimidines as inhibitors of immune-activated nitric oxide production》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(2-Amino-4,6-dichloro-5-methylpyrimidine)COA of Formula: C5H5Cl2N3.

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Kolman, Viktor; Kalcic, Filip; Jansa, Petr; Zidek, Zdenek; Janeba, Zlatko published the article 《Influence of the C-5 substitution in polysubstituted pyrimidines on inhibition of prostaglandin E2 production》. Keywords: pyrimidine preparation SAR prostaglandin E2 inhibitor; Inhibitor; Prostaglandin E(2); Pyrimidines; Suzuki-Miyaura reaction.They researched the compound: 2-Amino-4,6-dichloro-5-methylpyrimidine( cas:7153-13-1 ).Recommanded Product: 7153-13-1. 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:7153-13-1) here.

As a part of a broader structure-activity relationship study of substituted 2-aminopyrimidines, the influence of the C-5 substitution on inhibition of prostaglandin E2 (PGE2) production was studied. Thirty compounds were prepared starting from the corresponding 2-amino-4,6-dichloropyrimidines using Suzuki cross-coupling. It was shown previously that 2-amino-4,6-dichloropyrimidines with smaller C-5 substituent (hydrogen and methyl) were devoid of significant activity, while 5-Bu derivatives exhibited prominent potency. In this study, on the other hand, both monoaryl- and bisarylpyrimidines were potent inhibitors of PGE2 production regardless the length of the C-5 substituent (hydrogen, Me, n-butyl). Moreover, the shorter the C-5 substituent the higher potency to inhibit PGE2 production was observed 2-Amino-4,6-diphenylpyrimidine was the best inhibitor of PGE2 production with IC50 = 3 nM and no cytotoxicity. The most potent inhibitors deserve further preclin. evaluation as potential anti-inflammatory agents.

The article 《Influence of the C-5 substitution in polysubstituted pyrimidines on inhibition of prostaglandin E2 production》 also mentions many details about this compound(7153-13-1)Recommanded Product: 7153-13-1, you can pay attention to it or contacet with the author([email protected]; [email protected]) to get more information.

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Hull, R.; Lovell, B. J.; Openshaw, H. T.; Todd, A. R. published the article 《Synthetic antimalarials. XI. Effect of variation of substituents in derivatives of mono- and dialkylpyrimidines》. Keywords: MALARIA/therapy; PYRIMIDINES.They researched the compound: 2-Amino-4,6-dichloro-5-methylpyrimidine( cas:7153-13-1 ).Synthetic Route of C5H5Cl2N3. 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:7153-13-1) here.

cf. C.A. 41, 134b. Following the discovery that certain 2-amino-4-dialkylaminoalkylamino-5, 6-dialkylpyrimidines (C.A. 40, 5057.4) have marked antimalarial activity, a more extended investigation has been made of the effects of variation of substituents in compounds of this type; several other series of simple mono- and dimethylpyrimidine derivatives have been synthesized. 2-Amino-4-hydroxy-5-methylpyrimidine (m. 277-9°; preparation in 17% yield given) (5 g.) and 30 cc. POCl3, refluxed 45 min., give 68% 4-chloro-2-amino-5-methylpyrimidine, m. 184-5°; 4-(2-diethylaminoethylamino) analog, straw color, b. 170° (bath temperature)/3 × 10-4 mm. (dipicrate, yellow, m. 195-6°); 4-(3-diethylaminopropylamino) analog m. 70-1°. HCO2Et and PhOCH2CO2Et with Na in absolute Et2O, followed by guanidine, give 55% 2-amino-4-hydroxy-5-phenoxypyrimidine (I), m. 255-6°; 5 g. with POCl3 (refluxed 15 min.) gives 4.4 g. of the 4-Cl analog, m. 157.5°. I (3 g.), 1.53 cc. Ac2O, and 15 cc. anhydrous C5H5N, refluxed 2 h., give 2.05 g. of a compound, C24H20O5N6, m. 239-40°; with POCl3, 13.3 g. gives 13.5 g. 4-chloro-2-acetamido-5-phenoxypyrimidine (II), m. 163°. II (1.5 g.) and Et2N(CH2)2NH2, refluxed 5 h. and the product refluxed with 30 cc. 10% HCl 6 h., give 89% 2-amino-4-(2-diethylaminoethylamino)-5-phenoxypyrimidine, m. 114-15°; 4-(3-diethylaminopropylamino) homolog, m. 130.5-1°, 98%. Dropwise addition of 17 cc. Br to 40 g. 2-amino-4-hydroxy-6-methylpyrimidine in 350 cc. AcOH during 30 min. gives the 5-Br derivative, m. 250° (decomposition); POCl3 gives 79% 4-chloro-5-bromo-2-amino-6-methylpyrimidine, m. 206-7°; 4-(2-diethylaminoethylamino) analog, yellow viscous oil, b. 200°/10-2 mm. (bath temperature), 80%; 4-(3-diethylaminopropylamino) analog m. 105.5-7°, 91.5%. 4-Chloro-2,6-diaminopyrimidine (III) (preparation in 84% yield given) (5.78 g.) and 4.45 g Et2N(CH2)2NH2 in 13 cc. dry C5H5N, refluxed 16 h., give 62% 2,6-diamino-4-(2-diethylaminoethylamino)pyrimidine, b. 270°/10-3 (bath temperature) (dipicrate, m. 204-6°); the 4-(3-diethylaminopropylamino) homolog b. 250°/10-3 (dipicrate, m. 202.-3°). III (6.5 g.) and 20.8 g. Et2N(CH2) 2NH2, refluxed 6 h., give 9.25 g. (crude) 2-amino-4,6-bis(2-diethylaminoethylamino) pyrimidine, m. 58-60° (picrate m. 177.5-8.5°); this results also from 4-chloro-2-amino-6-(2-diethylaminoethylamino)pyrimidine and Et2N(CH2)2NH2 on heating 6 h. at 150°; 4,6-bis(3-diethylaminopropylamino) homolog b. 270°/4 × 10-4 mm. (bath temperature). 4-Chloro-2,6-diamino-5-methylpyrimidine gives 88% of the 4-(2-diethylaminoethylamino) analog, m. 102°, and 81% of the 4-(3-diethylaminopropylamino) analog, yellow, b. 250-70°/10-2 mm. (bath temperature) [bis-(3,5-dinitrobenzoate), m. 213°], which forms a hygroscopic, waxy solid. 4,6-Dichloro-2-amino-5-methylpyrimidine (9.0 g.) and 5.8 g. Et2N(CH2) 2NH2 in 25 cc. C5H5N, refluxed 15 h., give 55% 4-chloro-2-amino-6-(2-diethylaminoethylamino)-5-methylpyrimidine, m. 99-101°; 6-(3-diethylaminopropylamino) homolog, m. 121-2°, results in 76% yield on heating the components in AcOH 4 h. at 110° and 2 h. at 130°. 4-Hydroxy-2-methylmercapto-5,6-dimethylpyrimidine (IV) and POCl3, warmed 5 min. on the steam bath, give 92% of the 4-Cl analog, m. 35-6°; an excess saturated anhydrous EtOH-NH3 6 h. at 115-25° gives 50% 4-amino-2-methylmercapto-5,6-dimethylpyrimidine (V), m. 158-9.5°. V (5.6 g.) and 8.6 g. Et2N (CH2)3NH2, heated 22 h. at 200-10°, give (after repeated distillation) 39% 4-amino-2-(3-diethylaminopropylamino)-5,6-dimethylpyrimidine, a viscous oil [bis-(3,5-dinitrobenzoate), pale yellow, m. 210-12°]. IV (5.7 g.) and 4.3 g. Et2N(CH2)2NH2, heated 3 h. at 160-70°, give 98% 2-(2-diethylaminoethylamino)-4-hydroxy-5,6-dimethylpyrimidine, m. 86.5-8°; POCl3 gives 81% of the 4-Cl analog, m. 46.5-7.5°, sublimes 90°/10-4 mm., which with saturated EtOH-NH3 (3 h. at 180-90°) yields 49% 4-amino-2-(2-diethylaminoethylamino)-5,6-dimethylpyrimidine, m. 130-1.5°; this results also from 0.85 g. V and 2.3 g. Et2N(CH2)2NH2 on heating 22 h. at 190-200°. 2-(3-Dibutylaminopropylamino)-4-hydroxy-5,6-dimethylpyrimidine was a pale yellow oil, b. 260-80°/2 × 10-4 mm. (bath temperature), which slowly solidified (96%) (dipicrate, m. 199-202°); POCl3 gives the 4-Cl analog, b. 185-90°/4 × 10-3 mm. (bath temperature) (dipicrate, bright yellow, m. 167.5-8.5°); EtOH-NH3 (4 h. at 200°) gives 74% of the 4-NH2 analog, yellow oil, b. 210-20°/2 × 10-3 mm. (bath temperature) (dipicrate, yellow, m. 167-9°). 2-(3-Dimethylaminopropylamino)-4-hydroxy-5,6-dimethylpyrimidine m. 113.5-15°; 4-Cl analog m. 36-8°, 55%; 4-NH2 analog, yellow, b. 180-90°/2 × 10-3, 28% (tartrate, m. 168-71°). The following 2-substituted 4-amino-6-methylpyrimidines were prepared from the appropriate 4-Cl derivatives (C.A. 40, 5060.6): 3-dimethylaminopropylamino (VI) as the bis(3,5-dinitrobenzoate), m. 223-5°; 2-diethylaminoethylamino, m. 98-100°; 3-diethylaminopropylamino as the bis(3,5-dinitrobenzoate), m. 218-20°; 3-dibutylaminopropylamino as the bis(3,5-dinitrobenzoate), m. 200-2°. 4-Chloro-2-methylmercapto-6-methylpyrimidine and concentrated EtOH-NH3, 5.5 h. at 125-35°, give 74% 4-amino-2-methylmercapto-6-methylpyrimidine, m. 133.5-5°; with Me2N(CH2)3NH2 (14 h. at 160-70°) this yields 93% VI. 4-Substituted 6-amino-2,5-dimethylpyrimidines: 2-diethylaminoethylamino, m. 82-2.5°; 3-dimethylaminopropylamino, m. 89-91° [bis(3,5-dinitrobenzoate) , m. 207.5-9°]; 3-diethylaminopropylamino, m. 99.5°. 4-Substituted 6-amino-5-methylpyrimidines: 2-diethylaminoethylamino, m. 95.5-6.5°; 3-diethylaminopropylamino, m. 93-4°. HC(:NH)NH2.HCl (42 g.) and 91 g. MeCH(CO2Et)2, added successively to 24.5 g. Na in 360 cc. EtOH at 20-5°, kept overnight at room temperature, and boiled 1 h., give 61% 4,6-dihydroxy-5-methylpyrimidine, decompose 320°; refluxed with POCl3 40 min., there results 66% 4,6-dichloro-5-methylpyrimidine, m. 56.5-7.5°; with EtOH-NH3 at 140° (3 h.) this yields 4-chloro-6-amino-5-methylpyrimidine, m. 237-8°. 5-Amino-4-hydroxy-2,6-dimethylpyrimidine (VII) (13.5 g.) in 75 cc. 98% HCO2H, refluxed 15 min., gives 92% 5-formamido-4-hydroxy-2,6-dimethylpyrimidine (VIII), m. 238-9° (decomposition); 9 g. VIII, added to 75 cc. ice-cold POCl3 and followed (below 50°) with 20 cc. PhNMe2 (3-4 cc. portions), gives 45% of the 4-Cl analog, m. 158-9.5°; ice-cold concentrated HCl gives 85% 4-chloro-5-amino-2,6-dimethylpyrimidine, m. 79-80°; 4-(3-diethylaminopropylamino) analog m. 68-70°, 78%; 4-(2-diethylaminoethylamino) analog m. 95-6°, 64%; 4-(3-dibutylaminopropylamino) analog, pale yellow oil, b. 230-40°/0.25 mm. (bath temperature). VII (6.2 g.) in 220 cc. Ac2O, heated on the steam bath 30 min., gives 88% of the 5-acetamido derivative, m. 275° (decomposition); POCl3 gives 54% 4-chloro-5-acetamido-2,6-dimethylpyrimidine, m. 141-2°; 4-(3-diethylaminopropylamino) analog (IX), pale yellow oil, b. 150-60°/10-4 (bath temperature) (flavianate-1H2O, bright yellow, m. 160°). IX (5.5 g.) in 30 cc. 30% H2SO4, heated 2 h. on the steam bath, gives 9-(3-diethylaminopropyl)-2,6,8-trimethylpurine, pale yellow, b. 140-50°/10-4 mm. (bath temperature) (dipicrate, pale yellow, m. 187-8°); the 2-diethylaminoethyl homolog, pale yellow, b. 130-5°/2 × 10-3 mm. (bath temperature) (flavianate, bright yellow, m. 248° (decomposition)); 3-diethylamino-1-methylbutyl analog b. 150-5°/10-4 mm. (bath temperature) (a crystalline derivative could not be prepared). Guanidine and PhN2CHAc2 in EtOH, kept 20 days at room temperature, give 58.5% 2-amino-5-phenylazo-4,6-dimethylpyrimidine (X), bright orange, m. 228-30°; reduction in absolute EtOH over Pd-BaSO4 at 90° and 75 atm. gives 100% 2,5-diamino-4,6-dimethylpyrimidine (XI), m. 183.5-4.5°. XI (8 g.) and 19.6 g. Et2N(CH2)2Cl in 40 cc. anhydrous C5H5N, refluxed 7 h., give 26% 2-amino-5-(2-diethylaminoethylamino)-4,6-dimethylpyrimidine, m. 95-6.5°; dipicrate, yellow, m. 187-9° (decomposition). X (1.1 g.) and 0.6 g. NaNH2 in 10 cc. PhMe, refluxed 10 h., treated with 8.8 g. Et2N(CH2)2Cl, and the refluxing continued 18 h. (160-70°), give 58% 2-(2-diethylaminoethylamino)-5-phenylazo-4,6-dimethylpyrimidine, red, m. 87-8°; catalytic reduction in EtOH over Pt oxide at room temperature and atm. pressure give 60% 5-amino-2-(2-diethylaminoethylamino)-4,6-dimethylpyrimidine, yellow oil, b. 160°/2 × 10-3 mm. (bath temperature) (dipicrate, bright yellow, m. 185-6°). H2NC(SMe):NH.HI (33 g.) and 18 g. Et2N(CH2)2NH2 in 150 cc. EtOH, refluxed 2 h., give 50% 2-diethylamino-ethylguanidine-2HI, m. 140-2°. 4-Amino-6-(3-diethylaminopropylamino)-2,5-dimethylpyrimidine is the most active of the simple pyrimidines prepared, appreciable activity being observed at a dose of 20 mg./kg. Data are given for the other compounds described above. No generalizations can be made about structure and antimalarial activity, but the most active compounds have structures which are compatible with the hypothetical mode of action advanced in Part III (C.A. 40, 5057.4). It is clearly impossible to argue the validity of any concept of action based on interference with the synthesis or functioning of enzyme components in the absence of extensive biol. investigations, but there would seem to be some justification for its retention as a basis for future work.

As far as I know, this compound(7153-13-1)Synthetic Route of C5H5Cl2N3 can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Amino-4,6-dichloro-5-methylpyrimidine(SMILESS: CC1=C(N=C(N)N=C1Cl)Cl,cas:7153-13-1) is researched.Safety of 3-Hydroxy-3-phenylpropanenitrile. The article 《Structure-Activity Studies on a Series of a 2-Aminopyrimidine-Containing Histamine H4 Receptor Ligands》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:7153-13-1).

A series of 2-aminopyrimidines, e.g. I (R1 = H, Me, OMe, NH2, Ph; R2 = H, Cl, I, NHMe, NMe2, Ph, 2-MeOC6H4, 1-naphthyl, 4-pyridyl, etc.), was synthesized as ligands of the histamine H4 receptor (H4R). Starting from a pyrimidine hit that was identified in an HTS campaign, SAR studies were carried out to optimize the potency, which led to compound I (R1 = H; R2 = t-Bu). This compound was further studied by systematically modifying the core pyrimidine moiety, the methylpiperazine at position 4, the NH2 at position 2, and positions 5 and 6 of the pyrimidine ring. The pyrimidine 6 position benefited the most from this optimization, especially in analogs in which the 6-tert-Bu was replaced with aromatic and secondary amine moieties. The highlight of the optimization campaign was compound I (R1 = H; R2 = 4-NCC6H4), which was potent in vitro and was active as an anti-inflammatory agent in an animal model and had antinociceptive activity in a pain model, which supports the potential of H4R antagonists in pain.

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Quality Control of 2-Amino-4,6-dichloro-5-methylpyrimidine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Amino-4,6-dichloro-5-methylpyrimidine, is researched, Molecular C5H5Cl2N3, CAS is 7153-13-1, about 5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines. Synthesis and inhibitory effects on immune-activated nitric oxide production. Author is Jansa, Petr; Holy, Antonin; Dracinsky, Martin; Kolman, Viktor; Janeba, Zlatko; Kostecka, Petra; Kmonickova, Eva; Zidek, Zdenek.

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, was developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biol. properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irresp. of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC50 of 2 μM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 μM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells.

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Application In Synthesis of 2-Amino-4,6-dichloro-5-methylpyrimidine. 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-Amino-4,6-dichloro-5-methylpyrimidine, is researched, Molecular C5H5Cl2N3, CAS is 7153-13-1, about Discovery of a Dual Tubulin Polymerization and Cell Division Cycle 20 Homologue Inhibitor via Structural Modification on Apcin.

Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biol. evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f(I) was much more efficient than the pos. compound apcin in inhibiting cancer cell growth, but it had approx. the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new anticancer therapeutics.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Pure quadrupole resonance determinations of molecular charge distributions. II. Substituted pyrimidines》. Authors are Hooper, H. O.; Bray, P. J..The article about the compound:2-Amino-4,6-dichloro-5-methylpyrimidinecas:7153-13-1,SMILESS:CC1=C(N=C(N)N=C1Cl)Cl).Name: 2-Amino-4,6-dichloro-5-methylpyrimidine. Through the article, more information about this compound (cas:7153-13-1) is conveyed.

cf. C.A. 52, 7796a. The amount of double-bond character of the C-Cl bond at the 2, 4, and 6 positions was estimated from the Cl pure quadrupole resonance frequencies for the following compounds: 4-amino-6-chloro-2-methylthiopyrimidine, 6-chloro-2,4-dimethoxypyrimidine, 2,4-diamino-6-chloropyrimidine, 4,6-dichloropyrimidine, 2,4-dichloro-6-methylpyrimidine, 2,4-dichloro-5-methylpyrimidine, 2,4-dichloropyrimidine, 2,4,6-trichloropyrimidine, 2,4,5,6-tetrachloropyrimidine, 2-amino-4-chloro-6-methylpyrimidine, 2-amino-4,6-dichloro-5-methylpyrimidine, and 2-amino-5-chloropyrimidine-4-carboxylic acid. If it is assumed that the N’s have a weak inductive effect on adjacent ring positions, the calculated values for the amount of double-bond character agree well with data obtained from experiments with Zeeman splitting techniques applied to pure quadrupole resonance spectra.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Amino-4,6-dichloro-5-methylpyrimidine(SMILESS: CC1=C(N=C(N)N=C1Cl)Cl,cas:7153-13-1) is researched.Electric Literature of C17H18Cl2N2. The article 《Combining Quantum Mechanical Ligand Conformation Analysis and Protein Modeling to Elucidate GPCR-Ligand Binding Modes》 in relation to this compound, is published in ChemMedChem. Let’s take a look at the latest research on this compound (cas:7153-13-1).

2-Aminopyrimidine ligands with flexible and rigid side chains was synthesized to investigate the role of ligand conformation in H4R ligand binding. The ligand binding conformations and orientations in the H4R binding pocket was elucidated. The combined ligand- and protein-ligand modeling method can be used as a general approach to investigate the binding modes of flexible side chains of ligands with other protein targets.

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