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[ CAS No. 146-77-0 ] {[proInfo.proName]}

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Chemical Structure| 146-77-0
Chemical Structure| 146-77-0
Structure of 146-77-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 146-77-0 ]

CAS No. :146-77-0 MDL No. :MFCD00005734
Formula : C10H12ClN5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :BIXYYZIIJIXVFW-UUOKFMHZSA-N
M.W :301.69 Pubchem ID :8974
Synonyms :
2-Chloroadenosine

Calculated chemistry of [ 146-77-0 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 4.0
Molar Refractivity : 67.68
TPSA : 139.54 Ų

Pharmacokinetics

GI absorption : Low
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) : -8.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : -0.37
Log Po/w (WLOGP) : -1.64
Log Po/w (MLOGP) : -2.16
Log Po/w (SILICOS-IT) : -1.72
Consensus Log Po/w : -0.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.68
Solubility : 6.33 mg/ml ; 0.021 mol/l
Class : Very soluble
Log S (Ali) : -2.1
Solubility : 2.41 mg/ml ; 0.00799 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.19
Solubility : 193.0 mg/ml ; 0.64 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.9

Safety of [ 146-77-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P201-P202-P281-P308+P313-P405-P501 UN#:N/A
Hazard Statements:H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 146-77-0 ]

* 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 [ 146-77-0 ]
  • Downstream synthetic route of [ 146-77-0 ]

[ 146-77-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 146-77-0 ]
  • [ 1839-18-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1135 - 1140
[2] Patent: WO2006/81665, 2006, A1, . Location in patent: Page/Page column 26-27
  • 2
  • [ 146-77-0 ]
  • [ 77-76-9 ]
  • [ 24639-06-3 ]
YieldReaction ConditionsOperation in experiment
88% With perchloric acid In water at 20℃; for 8 h; Inert atmosphere [0042] Under N2(g), 2-chloroadenosine (Ila, 20 g, 66.3 mmol), 2,2-dimethoxypropane (DMOP, 60 mL) and aqueous HCIO4 (70percent wt, 3 mL) was stirred at room temperature for 8 h. The pH of the reaction mixture was slowly adjusted with a saturated aq. NaHC03 (ca.120 mL) to 7-9. After stirring in ice bath for 2 h, the mixture was filtered, washed with water (50 mL) and then dried under vacuum at 50°C for 6 h to afford the compound of formula lib with 99percent purity in 88percent yield. [0043] 1H NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), δ 7.87 (s, 2H), δ 6.06 (d, J = 2.4 Hz, 1H), δ 5.28 (dd, J =6 Hz, 2.4 Hz, 1H), δ 5.08 (t, J = 5.6 Hz, 1H), δ 4.94 (dd, J = 6 Hz, 2 Hz, 1H), δ 4.21 (m, 1H), δ 3.54 (m, 2H, ), δ 1.54 (s, 3H), δ 1.33 (s, 3H). [0044] 13C NMR (100 MHz, DMSO-d6) δ 157.3, 153.6, 150.4, 140.4, 1 18.6, 1 13.6, 89.8, 87.2, 83.9, 81.7, 62.0, 27.5, 25.7.
Reference: [1] Nucleosides and Nucleotides, 1999, vol. 18, # 10, p. 2175 - 2191
[2] Patent: WO2015/85497, 2015, A1, . Location in patent: Paragraph 0041-0044
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4556 - 4560
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 85 - 89
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 1919 - 1924
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 2916 - 2919
[7] Journal of the American Chemical Society, 2014, vol. 136, # 9, p. 3370 - 3373
  • 3
  • [ 146-77-0 ]
  • [ 67-64-1 ]
  • [ 24639-06-3 ]
YieldReaction ConditionsOperation in experiment
83% at 20℃; for 22 h; Cooling with ice; Inert atmosphere A mixture of p-toluenesulfonic acid (PTSA) (1.72g, 10mmol) and dry acetone (20ml) was added dropwise into a stirring mixture of 2-chloro-adenosin (309mg, 1mmol) and dry acetone (20ml) in ice-water bath. The mixture was stirred at room temperature for 22h and then was poured into ice sodium bicarbonate solution (4percent w.t.) with stirring until the bubble disappeared. The liquid was then extracted with CH2Cl2 for three times. The organic layers were dried over anhydrous MgSO4 and concentrated to afford a faint yellow solid 7 (283mg, 83percent). 1H NMR (400MHz, DMSO-d6): δ=8.37 (s, 1H, imidazole-H), 7.89 (br., 2H, NH2), 6.06 (d, J=2.4Hz, 1H, 1′-H), 5.28–5.30 (m, 1H, 2′-H), 5.10–5.12 (m, 1H, OH), 4.93–4.95 (m, 1H, 3′-H), 4.21–4.23 (m, 1H, 4′-H), 3.54–3.57 (m, 2H, 5′-H), 1.55 (s, 3H, CH3), 1.33ppm (s, 3H, CH3); HRMS (ESI) m/z [M+H]+ calcd. for C13H17ClN5O4: 342.0969, found: 342.0968.
83% at 20℃; for 22 h; Cooling with ice A mixture of 2-chloro-adenosine 309mg (1mmol) was dissolved in 10 ~ 30ml (preferably 20 ml) of acetone, p-toluenesulfonic acid 8 ~ 12mmol (preferably 10 mmol) was dissolved in 10 ~ 30ml (preferably 20 ml) of acetone. Acetone solution under ice-water bath and p-toluenesulfonic acid acetone solution was slowly dropped into 2-chloro-adenosine, and stirred at room temperature 12 ~ 36 h (preferably 22h). The reaction mixture was poured into 4percent aqueous sodium bicarbonate and ice, and extracted with methylene chloride, the organic layer was collected, dried over magnesium sulphate, filtered and concentrated to afford the product as a white powder after drying, a yield of 83percent.
82% With sulfuric acid In water at 20℃; for 2 h; Inert atmosphere [0086] Under N2(g), 2-chloroadenosine (Ila, 10 g, 33.15 mmol), acetone (200 mL) and cone. H2SO4 (98percent wt, 5 mL) was stirred at room temperature for 2 h. The pH of the reaction mixture was slowly adjusted with a saturated aq. NaHC03 to 7-9. DCM (200 mLx2) was used to extract the aqueous phase twice. The combined organic phase was washed with brine (100 mL) and then dried with anhydrous Na2S04. The isolated dried organic phase was evaporated under vacuum at 50°C to give suspension. The mixture was filtered and dried to afford the compound of Formula lib with 99percent purity in 82percent yield.
Reference: [1] Journal of Photochemistry and Photobiology B: Biology, 2016, vol. 159, p. 196 - 204
[2] Patent: CN103435639, 2016, B, . Location in patent: Paragraph 0081; 0082
[3] Patent: WO2015/85497, 2015, A1, . Location in patent: Paragraph 0086
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 6, p. 1087 - 1092
[5] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 50
[6] Chemical Biology and Drug Design, 2018, vol. 91, # 2, p. 552 - 566
[7] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 50
  • 4
  • [ 146-77-0 ]
  • [ 104-15-4 ]
  • [ 24639-06-3 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 4 h; Inert atmosphere To an adenosine 3 (1.0 g, 3.74 mmol, 1 equiv) in acetone (30 mL/mmol) was added dry tosylic acid (10 equiv) at room temperature under an argon atmosphere. The resulting mixture was stirred at room temperature for 4 h. After completion of reaction (indicated by TLC), the reaction mixture was cooled to 0 °C and sat. aq. NaHCO3 solution added until the pH of the mixture became slightly basic. Acetone was evaporated under reduced pressure and the residue was extracted in EtOAc (3 × 30 mL). The combined organic fractions were washed with brine (1 × 15 mL), dried over MgSO4 and evaporated under reduced pressure to afford the title compound 5 as white solid (0.625g, 54percent). Rf = 0.45 (10percent MeOH in DCM). Mp = 228−230 °C. 1H NMR (500 MHz, DMSO-d6) δH = 8.34 (s, 1H, HAr), 8.16 (s, 1H, HAr), 7.35 (bs, 2H, Ar-NH2), 6.12 (d, J = 3.1 Hz, 1H, CHribose), 5.34 (dd, J = 6.4, 3.1 Hz, 1H, CHribose), 5.24 (bs, 1H, 5-OH), 4.96 (dd, J = 6.15, 2.45 Hz, 1H, CHribose), 4.23-4.20 (m, 1H, CHribose), 3.58-3.51 (m, 2H, 5-CH2), 1.54 (s, 3H, CH3), 1.32 (s, 3H, CH3), general assignments were confirmed by 1H-1H gCOSY. 13C NMR (125 MHz, DMSO-d6) δC = 156.1 (Cquat), 152.6 (Cquat), 148.8 (Cquat), 139.7 (CHAr), 119.1 (Cquat), 113.0 (CHAr), 89.6 (CHribose), 86.4 (CHribose), 83.2 (CHribose), 81.4 (CHribose), 61.6 (5-CH2), 27.1 (CH3), 25.2 (CH3), general assignments were confirmed by 1H-13C HSQC. LRMS (ESI): 330 [M + Na]+, HRMS (ESI): calcd for [C13H17N5O4 + Na]+ 330.1172, found 330.1169
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 3009 - 3013
  • 5
  • [ 146-77-0 ]
  • [ 77-76-9 ]
  • [ 67-64-1 ]
  • [ 24639-06-3 ]
Reference: [1] Patent: WO2008/157438, 2008, A1, . Location in patent: Page/Page column 13; 22
  • 6
  • [ 146-77-0 ]
  • [ 72209-19-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 1919 - 1924
[2] Journal of the American Chemical Society, 2014, vol. 136, # 9, p. 3370 - 3373
  • 7
  • [ 146-77-0 ]
  • [ 124431-80-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 1919 - 1924
  • 8
  • [ 146-77-0 ]
  • [ 123318-82-1 ]
Reference: [1] Patent: US2017/44204, 2017, A1,
[2] Patent: US2017/44204, 2017, A1,
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