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Chemical Structure| 4016-63-1 Chemical Structure| 4016-63-1
Chemical Structure| 4016-63-1

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8-Bromoguanosine is a brominated derivative of guanosine.

Synonyms: 2-Amino-8-bromo-6-hydroxypurine riboside; NSC 174257; NSC 79211

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Product Details of 8-Bromoguanosine

CAS No. :4016-63-1
Formula : C10H12BrN5O5
M.W : 362.14
SMILES Code : O=C1NC(N)=NC2=C1N=C(Br)N2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
Synonyms :
2-Amino-8-bromo-6-hydroxypurine riboside; NSC 174257; NSC 79211
MDL No. :MFCD00037985
InChI Key :ASUCSHXLTWZYBA-UMMCILCDSA-N
Pubchem ID :135465599

Safety of 8-Bromoguanosine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 8-Bromoguanosine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4016-63-1 ]

[ 4016-63-1 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 108-24-7 ]
  • [ 4016-63-1 ]
  • [ 15717-45-0 ]
YieldReaction ConditionsOperation in experiment
85% With dmap; triethylamine; In acetonitrile; at 20℃; for 0.5h; Compound 13 (11.0 g, 30.4 mmol) and 4-dimethylaminopyridine (296.9 mg, 2.4 mmol) were dissolved in 100 mL acetonitrile. After slow addition of triethylamine (16.7 mL, 120.0 mmol) and Ac2O (10.0 mL, 106.3 mmol), the mixture continued to stir at room temperature for 30 min. The reaction was quenched by addition of 5 mL MeOH and then the solvent was evaporated in vacuo. The residue was recrystallized from the mixture of 2-propanol and water (v/v, 1:7) to afford 14 as white powder (12.6 g, 85percent), mp 192-196 °C; 1H NMR (400 MHz, CDCl3): delta 11.70 (1H, s), 6.57 (2H, s), 6.37 (1H, s), 6.02 (1H, d, J = 5.2 Hz), 5.96 (1H, d, J = 3.6 Hz), 4.50 (1H, m), 4.34 (2H, t, J = 6.4 Hz), 2.16 (3H, s), 2.14 (3H, s), 2.03 (3H, s). 13CNMR (100 MHz, CDCl3): delta 170.8, 169.6, 169.5, 157.6, 153.7, 152.3, 121.6, 117.7, 88.4, 79.7, 72.2, 70.4, 62.9, 20.7, 20.6, 20.5.
  • 2
  • [ 67-56-1 ]
  • [ 4016-63-1 ]
  • [ 7057-53-6 ]
  • 5
  • [ 51688-22-3 ]
  • [ 4016-63-1 ]
  • [ 96412-43-0 ]
  • 6
  • [ 4016-63-1 ]
  • [ 124-40-3 ]
  • [ 7057-52-5 ]
  • 7
  • [ 4016-63-1 ]
  • [ 107-18-6 ]
  • [ 126138-81-6 ]
YieldReaction ConditionsOperation in experiment
51% To a solution of prop-2-en-1-ol (120 ml) in DMSO (160 mL, anhydrous) was added sodium hydride (1 lg, 276 mmol) in portions at 0 oC. The mixture was allowed to warm to 25°C with stirring for lh, and then 2-amino-8-bromo-9-((2R,3R,4S,5R)-3,4- dihydroxy-5 -(hydroxymethyl)-tetrahydrofuran-2-yl)- 1H-purin-6(911)-one was added. The mixture was stuffed for 0.5h and then heated to 60°C with stirring for 4 hours. Themixture was allowed to cooled to r.t. and then added to diethyl ether (2.5 L) to give a gray precipitate and purified by reverse phase biotage to give a white solid product(4.8g , 51percent).LC-MS: CP-0007023-020: (ES, nz/z): 340 [M+ Hj
  • 8
  • [ 4016-63-1 ]
  • [ 106-95-6 ]
  • [ 126092-30-6 ]
  • 9
  • [ 4016-63-1 ]
  • [ 106-95-6 ]
  • [ 137616-58-1 ]
  • 10
  • [ 4016-63-1 ]
  • [ 74-89-5 ]
  • [ 13389-05-4 ]
  • 12
  • [ 4016-63-1 ]
  • [ 22423-08-1 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; In ethanol; water; at 100℃; for 4h;Microwave irradiation; 8-Hydrazinoguanosine 3 was prepared following the described procedure[29] in 51% yield and under modified conditions using microwave irradiationin 75% yield. To a solution of hydrazine monohydrate (780 lL,10 mmol, 98% with 64 - 65% hydrazine) in the EtOH/H2O mixture(12.4 mL, 30:1 v/v) <strong>[4016-63-1]8-bromoguanosine</strong> 3 (362 mg, 1 mmol) was added and the suspension was stirred in a borosilicate glass vial at 100 C for 4 h in the microwave cavity. After cooling to 55 C obtained fluffy precipitate was filtered off under argon atmosphere and dried under vacuum protected from light to give 8-hydrazinoguanosine 3 (235.3 mg, 75%) as a light blue powder homogeneous by TLC: mp >237 C dec (lit.[29]>238 C dec;lit.[30]>240 C dec); Rf = 0.5 (CH2Cl2/MeOH 3:1); UV (MeOH): lambdamax/nm 261, log epsilon/dm3mol-1cm-1 3.61; IR (KBr) nu/cm-1: 3421 (s), 2920 (m), 1701(m), 1686 (m), 1678 (m), 1655 (m), 1637 (m), 1601 (m), 1578 (m), 1572(m), 1560 (m), 1555 (w), 1491 (w), 1458 (w), 1419 (w), 1126 (w), 1092 (w),1070 (w), 1041 (w); 1H NMR (DMSO-d6) delta/ppm: 11.00 (bs, 1H, NH-1), 7.31 (bs, 3H, NHNH2), 6.22 (bs, 2H, NH2), 5.70 (d, 1H, J 8.5 Hz, H-1'),5.60 (bs, 1H, OH-5'), 5.21 (bd, 1H, OH-2'(OH-3')), 5.01 (bs, 1H, OH-3'(OH-2')), 4.47 (m, 1 H, H-2'), 4.05 (m, 1 H, H-3'), 3.84 (m, 1 H, H-4'),3.59 (m, 2 H, H-5a', H-5b'); 13C NMR (DMSO-d6) delta/ppm: 155.7 (C-6),153.7 (C-2), 152.3 (C-4), 151.4 (C-8), 112.2 (C-5), 85.9 (C-1'), 85.1 (C-4'),70.7 (C-2'(C-3')), 70.2 (C-3'(C-2')), 61.1 (C-5'). The obtained compound isunstable exposed to air and light. Because of rapid decomposition in solution,crude product is used in the next synthetic step without furtherpurification.
  • 13
  • [ 4016-63-1 ]
  • [ 129662-42-6 ]
  • 14
  • [ 4016-63-1 ]
  • [ 13389-07-6 ]
  • 16
  • [ 4016-63-1 ]
  • [ 58-63-9 ]
  • 2-(8-guanosyl)inosine [ No CAS ]
  • 17
  • [ 4016-63-1 ]
  • [ 146-80-5 ]
  • 8-(8-guanosyl)xanthosine [ No CAS ]
  • 21
  • [ 118-00-3 ]
  • [ 4016-63-1 ]
YieldReaction ConditionsOperation in experiment
85% With bromine; In water; To a suspension of guanosine 5 (4.0 g, 14.4 mmol) in water (100 mL) was added bromine (0.8 mL, 14.6 mmol) at such a rate that reaction mixture became colourless between each addition. The addition was stopped when the reaction mixture stayed slightly yellow due to unreacted bromine. The colourless solid was quickly filtered off, washed with 60 mL of cold water and 30 mL of cold acetone, recrystallized from 150 mL of hot water and dried in vacuo for 6 h at 60 C. Yield 4.4 g (11.8 mmol, 85%) of colourless, needle-shaped crystals 13, mp 198-200 C; 1H NMR (400 MHz, DMSO-d6): delta 10.82 (1H, s), 6.50 (2H, s), 5.69 (1H, d, J = 6.4 Hz), 5.45 (1H, d, J = 6.0 Hz), 5.09 (1H,d, J = 5.2 Hz), 5.02 (1H, dd, J = 6.0, 11.6 Hz), 4.92 (1H, t, J= 6.0 Hz), 4.14 (1H, m), 3.86 (1H, m), 3.66 (1H, m), 3.52 (1H, m). 13C NMR (100 MHz, DMSO-d6): delta 155.5, 153.4, 152.0, 121.2, 117.5, 89.7, 85.8, 70.5, 70.3, 62.0.
51% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In N,N-dimethyl-formamide; at 25℃; for 2.5h; Typical procedure for the bromination of unprotected nucleosides: DBH (323 mg, 1.13 mmol) was added to a stirred solution of 1d (500 mg, 2.05 mmol) in DMF (5 mL). The resulting pale-yellow solution was stirred at room temperature for 20 minutes or until TLC showed absence of starting material and formation of less polar product. Volatiles were evaporated and the residue was coevaporated with MeCN. The resulting pale solid was crystallized from hot acetone to give 2d (500 mg, 75%) as colorless crystals with data as reported.14
15% With sodium azide; bromoisocyanuric acid monosodium salt; In water; N,N-dimethyl-formamide; at 20℃; for 0.5h; General procedure: 5'-O-Monomethoxytrityl-N2-phenoxyacetylguanosine (33, 0.138 g, 0.2 mmol) was dissolved inaqueous DMF solution (H2O:DMF 1:4, 5 mL) under stirring. SMBI (1.1 equiv., 0.051 g, 0.22 mmol)was added at r.t. and the mixture stirred. Progress of the reaction was followed by TLC. An additionalamount of the reagent (0.15 equiv., 0.007 g) was added into the reaction mixture after 1.5 h. Oncompletion of the reaction by 2 h, the reaction mixture was filtered, evaporated to dryness underreduced pressure and coevaporated with water (2 × 2 mL). The crude reaction mixture was purified bycolumn chromatography (4%-5% MeOH in DCM, v/v) to afford nucleoside 34 (0.148 g, 96%) in pureform as a white solid.8-Bromo-5'-O-monomethoxytrityl-N2-phenoxyacetylguanosine (34).
With N-Bromosuccinimide; In water; (1-1-1) Synthesis of 8-Styrylguanosine (Reference Numeral 6a of the Chem. 11) Ten grams of guanosine (reference numeral 1 in the chem. 11), 7.54 g of N-bromosuccinimide, and 500 mL of water were placed in an eggplant-shaped flask, and the mixture solution thus prepared was stirred for 2 hours at room temperature. After the reaction, resultant precipitate was filtered off to obtain 9.03 g of 8-bromoguanosine (reference numeral 2 in the chem. 11).

  • 22
  • [ 18395-90-9 ]
  • [ 4016-63-1 ]
  • 2-Amino-8-bromo-9-((4aR,6R,7R,7aS)-2,2-di-tert-butyl-7-hydroxy-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl)-1,9-dihydro-purin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
wherein the compound is selected from the group consisting of:...2-Chloroadenosine,9-(beta-D-Ribofuranosyl)purine,8-Bromoadenosine,8-Bromo-2'-deoxyadenosine,8-Bromoguanosine,6-Thioinosine,6-Methylthio-9-(beta-D-ribofuranosyl)purine,6-Chloro-9-(beta-D-ribofuranosyl)purine,...
Even further illustrative of the present invention is a method for inhibiting RNA-dependent RNA viral polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection wherein the compound is selected from...4-amino-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,4-amino-7-(2-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxmide,2'-C-methyladenosine,8-amino-2'-C-methyladenosine,8-bromoguanosine,8-aminoguanosine,8-aminoadenosine,4-amino-7-(3-deoxy-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine,...
Further illustrative of the invention is a method for inhibiting RNA-dependent RNA viral polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection wherein the compound is selected from:...2-amino-5-methyl-7-(2-O-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin4(3H)-one,8-azidoguanosine,8-bromoadenosine,8-aminoadenosine,8-bromoguanosine,3'-deoxy-3'-fluorocytidine,3'-deoxy-3'-fluoroguanosine,2-amino-4-chloro-7-(2-O-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-5-carbonitrile,...
Illustrative of the invention is a method for inhibiting RNA-dependent RNA viral polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection wherein the compound is selected from:...8-azidoguanosine,8-aminoguanosine,8-bromoadenosine,8-aminoadenosine,8-bromoguanosine,3'-deoxy-3'-fluorocytidine,3'-deoxy-3'-fluoroguanosine,4-amino-7-(3-deoxy-3-fluoro-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-5-carboxamide,...

  • 27
  • [ 122-39-4 ]
  • [ 4016-63-1 ]
  • 8-diphenylaminoguanosine [ No CAS ]
  • 28
  • [ 56-45-1 ]
  • [ 4016-63-1 ]
  • 8-(1-carboxy-2-hydroxyethylamino)guanosine [ No CAS ]
  • 31
  • [ 4016-63-1 ]
  • [ 147-85-3 ]
  • 8-(2-carboxycyclobutyl)aminoguanosine [ No CAS ]
  • 32
  • [ 4016-63-1 ]
  • [ 168701-80-2 ]
  • [ 80106-09-8 ]
  • 33
  • [ 4016-63-1 ]
  • [ 168701-80-2 ]
  • 8-nitroguanosine [ No CAS ]
  • [ 80106-09-8 ]
  • 34
  • [ 302-84-1 ]
  • [ 4016-63-1 ]
  • 8-(1-carboxy-2-hydroxyethylamino)guanosine [ No CAS ]
  • 35
  • [ 4016-63-1 ]
  • [ 609-36-9 ]
  • 1-[2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl]-pyrrolidine-2-carboxylic acid [ No CAS ]
  • 36
  • [ 110-86-1 ]
  • [ 4016-63-1 ]
  • [ 432550-45-3 ]
  • 37
  • [ 110-86-1 ]
  • [ 4016-63-1 ]
  • 1-(guanosin-8-yl)pyridinium bromide [ No CAS ]
  • 38
  • [ 108-89-4 ]
  • [ 4016-63-1 ]
  • C11H10N6O [ No CAS ]
  • 39
  • [ 108-89-4 ]
  • [ 4016-63-1 ]
  • 1-(guanosin-8-yl)-4-methylpyridinium bromide [ No CAS ]
  • 41
  • [ 1765-93-1 ]
  • [ 4016-63-1 ]
  • 8-(4-fluorophenyl)guanosine [ No CAS ]
  • 44
  • [ 563-63-3 ]
  • [ 108-24-7 ]
  • [ 4016-63-1 ]
  • Acetic acid 2-acetylamino-9-((2R,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl ester [ No CAS ]
  • 45
  • [ 2082-76-0 ]
  • [ 4016-63-1 ]
  • 2',3',5'-O-tridecanoyl-8-bromoguanosine [ No CAS ]
  • 46
  • [ 4637-24-5 ]
  • [ 4016-63-1 ]
  • 2N-((dimethylamino)methylene)-8-bromoguanosine [ No CAS ]
  • 47
  • [ 108-24-7 ]
  • [ 4016-63-1 ]
  • 2',3',5'-tri-O-acetyl-8-methoxyguanosine [ No CAS ]
  • 48
  • [ 873-73-4 ]
  • [ 4016-63-1 ]
  • 2-Amino-8-(4-chloro-phenylethynyl)-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one [ No CAS ]
  • 49
  • [ 705-31-7 ]
  • [ 4016-63-1 ]
  • 8-(4-trifluoromethylphenylethynyl)guanosine [ No CAS ]
  • 50
  • [ 41876-70-4 ]
  • [ 4016-63-1 ]
  • 8-(4-N,N-diethylaminophenylethynyl)guanosine [ No CAS ]
  • 51
  • [ 42472-69-5 ]
  • [ 4016-63-1 ]
  • 8-(4-acetylphenylethynyl)guanosine [ No CAS ]
  • 52
  • [ 4016-63-1 ]
  • [ 536-74-3 ]
  • 8-(2'-phenylethynyl)guanosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 110℃; for 18h;Product distribution / selectivity; General Experimental Procedure; A solution of <strong>[4016-63-1]8-bromoguanosine</strong> (520 mg, 1.5 mmol, 1 eqv.) in dry DMF (12 mL) was added to the substituted phenylacetylene (1.8 mmol, 1.2 eqv.) and dry triethylamine (0.63 mL, 4.5 mmol, 3 eqv.) in a vacuum dried Schlenk tube. PdCl2 (PPh3)2 (11 mg, 0.015 mmol, 1 mol percent) and CuI (6 mg, 0.030 mmol, 2 mol percent) were added and the reaction mixture was left to stir at 110° C. for 18 h, after which time it was allowed to cool to 40° C. and the DMF removed in vacuo to leave a brown solid. The solid was transferred to a sintered glass filter and was washed with boiling water (5.x.200 mL), EtOAc (5.x.25 mL) and diethylether (2.x.25 mL) yielding the product as a light cream solid (0.53 g, 91percent).Representative data for 8-(2'-phenylethynyl)guanosine: Mp 234-236° C. (decomp.); numax (DMSO solution)/cm-1 1695 (CO), 3126 and 3328 (NH), 3421 (OH); deltaH (400 MHz; DMSO-d6) 3.65 (1H, m), 3.88 (1H, m), 3.84 (1H, s), 4.19 (1H, s), 4.99 (2H, m), 5.15 (1H, br s), 5.50 (1H, d, J 6.4), 5.89 (1H, d, J 6.4), 6.62 (2H, s), 7.51 (3H, m), 7.64 (2H, m), 10.90 (1H, s); deltaC (128 MHz; DMSO-d6) 61.9, 70.4, 70.8, 79.4, 85.6, 88.2, 92.6, 117.5, 120.4, 128.9, 129.3, 129.9, 131.5, 151.1, 153.9, 156.0; m/z (FAB) MH+ 384 (2.5percent), 369, 354, 277, 185 (100percent); HRMS (MH+): 384.1299 (Calcd. for C18H18N5O5 384.1307).; Example 1Determining Optimum Synthesis Conditions Sonogashira alkynylation protocol for the cross-coupling of 1 with phenylacetylene 9a to give 5a (Equation 1, Scheme 1). Initially, standard conditions for Sonogashira alkynylation of 1 were selected from the literature (10 mol percent (Ph3P)2PdCl2, 10 mol percent CuI, 1.2 equiv. 9a and 3 equiv. Et3 N in DMF at 110° C. for 18 hours). This proved to be a generally ineffective protocol, affording the product in yields of ca. 20percent with poor purity (believed to be due to the uptake of Pd and/or Cu; the uptake was confirmed by X-ray photoelectron spectroscopy (XPS)), which led to optimisation of the conditions. Rapid Pd agglomeration and precipitation were thought to contribute to the low yields, which relates the optimal palladium concentration (vide supra).Lowering the amount of (Ph3P)2 PdCl2 to 5 mol percent and CuI to 10percent resulted in an improved yield (52percent). It was established that 1 mol percent (Ph3P)2 PdCl2 and 2 mol percent CuI proved the most effective catalyst/co-catalyst combination, affording the cross-coupled product in 95percent yield (after only 2 hours). Such a successful reaction means that this reaction is suitable for scale up.Under similar conditions, the acetate protected guanosine derivative 2 reacted with 9a to produce 6a in 88percent yield, which was more cumbersome to purify than 5a, as column chromatography on silica-gel was required (eluting with methanol/chloroform solvent mixtures (1:99, v/v).; Example 2Assessment of the Effect of Cu(I) on YieldsThe purity of 5a was also questionable at the higher Cu(I) loading; the solid is a light green colour, rather than an off-white, due to the presence of trace quantities guanosine derived copper complexes (bidentate coordination through N-1 and O-6). This has been confirmed by infra-red spectroscopic experiments, which show the expected carbonyl shifts (in frequency) from uncoordinated ligand to coordinated ligand. The increased catalytic activity can be explained to a certain extent by the production of higher concentrations of alkynylcuprate, although an alternative role could also be responsible for the rate enhancement vide infra.A further experiment was carried out, where it was determined that 1 mol percent PdCl2 and 2 mol percent CuI was an ineffective catalyst/co-catalyst combination, highlighting the importance of the activating phosphine ligand in the intimate steps of the catalytic cycle-it was noted that palladium nanoparticles were rapidly formed in this reaction.
  • 53
  • [ 4016-63-1 ]
  • [ 768-60-5 ]
  • 8-(4-Methoxyphenylethynyl)guanosine [ No CAS ]
  • 54
  • [ 5720-05-8 ]
  • [ 4016-63-1 ]
  • [ 79953-04-1 ]
 

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