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Chemical Structure| 936-05-0
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Product Details of [ 936-05-0 ]

CAS No. :936-05-0 MDL No. :MFCD00159675
Formula : C5H7N3O3 Boiling Point : -
Linear Structure Formula :NO2CCHNC(CH2OH)N(CH3) InChI Key :JSAQDPJIVQMBAY-UHFFFAOYSA-N
M.W : 157.13 Pubchem ID :557356
Synonyms :
Hydroxy Dimetridazole;2-Hydroxymethyl-1-methyl-5-Nitroimidazole
Chemical Name :(1-Methyl-5-nitro-1H-imidazol-2-yl)methanol

Calculated chemistry of [ 936-05-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.44
TPSA : 83.87 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.86
Log Po/w (XLOGP3) : -0.37
Log Po/w (WLOGP) : -0.33
Log Po/w (MLOGP) : -1.16
Log Po/w (SILICOS-IT) : -1.89
Consensus Log Po/w : -0.58

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.79
Solubility : 25.8 mg/ml ; 0.164 mol/l
Class : Very soluble
Log S (Ali) : -0.93
Solubility : 18.5 mg/ml ; 0.118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.01
Solubility : 159.0 mg/ml ; 1.01 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.29

Safety of [ 936-05-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 936-05-0 ]

* 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.

  • Upstream synthesis route of [ 936-05-0 ]
  • Downstream synthetic route of [ 936-05-0 ]

[ 936-05-0 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
62% at 140℃; for 48 h; In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 °C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO4) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62percent yield) as white powder; m.p. 117 °C.
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
[4] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[5] Patent: WO2014/205414, 2014, A1, . Location in patent: Paragraph 0298
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YieldReaction ConditionsOperation in experiment
59% With ammonia; potassium carbonate In methanol at 50℃; for 18 h; Cytarabine (243 mg, 1.0 mmol), 2-Chlorocarbonyloxymethyl-l-methyl-5- nitroimidazole (439 mg, 2.0 mmol), sodium bicarbonate (336 mg, 4.0 mmol) and DMA (10 mL) were stirred for 7 days. The suspension was filtered and the filtrate concentrated in vacuo. The resultant oil was triturated with DCM; the suspension was filtered, and the solid was washed with DCM then dried at the pump. The solid was dissolved in methanol and then adsorbed on to flash silica. Column chromatography, eluting with 33percent then 50percent methanol / DCM, furnished an off-white wax (53 mg, 12percent); TLC Rf=0.3, 10percent methanol / ethyl acetate. NMR (500Mhz, DMSO-d6, δ)7.98 (IH, s, HarH), 7.35 (IH, bs, HarH), 5.99 (IH, s, NCHO), 5.86 (IH, bs, HarH), 5.65 (IH, bs, OH), 5.47 (IH, bs, OH), 5.26 (2H, m, HarCH2O), 5.05 (IH, s, OH), 4.08 (IH, bs, CHOH), 3.95 (3H, s, NCH3), 3.90 (IH, bs, OCHCH2OH), 3.73 (IH, bs, CHOH), 3.62 (2H, m, CH2OH) ppm.The 2-chlorocarbonyloxymethyl-l-methyl-5-nitroimidazole used in the above synthesis was prepared as follows: 2-Hydroxymethyl-l-methyl-5-nitroimidazole (314 mg, 2.0 mmol) in THF (10 mL) was added to phosgene (4 mL, 8.0 mmol) and THF EPO <DP n="37"/>(15 mL) at O0C. The reaction was stirred for 16 h then the solvent was removed in vacuo. The crude chloroformate was used without further purification.2-Hydroxymethyl-l-methyl-5-nitroiniidazole was prepared as follows: Methanolic ammonia (3.6 mL, 25 mmol) was added to a suspension of ronidazole (5 g, 25 mmol) and methanol (25 mL). Potassium carbonate (1.75 g, 12.5 mmol) was added and the reaction mixture heated to 5O0C for 18 h. The solution was cooled to ambient temperature then partitioned (ethyl acetate and brine), the aqueous phase was extracted (ethyl acetate); the organic phases were combined, washed (water then brine) then dried in vacuo. The desired product was obtained as an orange solid (2.3 g, 59percent) and was used without further purification.
Reference: [1] Patent: WO2006/32921, 2006, A1, . Location in patent: Page/Page column 35-36
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  • [ 4750-57-6 ]
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Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2258 - 2265
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  • [ 3034-42-2 ]
  • [ 936-05-0 ]
Reference: [1] Patent: US4010176, 1977, A,
  • 5
  • [ 57434-36-3 ]
  • [ 936-05-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2258 - 2265
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  • [ 551-92-8 ]
  • [ 936-05-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2258 - 2265
  • 7
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  • [ 59729-37-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
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