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Chemical Structure| 5720-05-8
Chemical Structure| 5720-05-8
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Yuan, Gengyang ; Dhaynaut, Maeva ; Lan, Yu , et al. DOI: PubMed ID:

Abstract: Metabotropic glutamate receptor 2 (mGluR2) is a therapeutic target for several neuropsychiatric disorders. An mGluR2 function in etiology could be unveiled by positron emission tomography (PET). In this regard, 5-(2-fluoro-4-[11C]methoxyphenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-7-carboxamide ([11C]13, [11C]mG2N001), a potent negative allosteric modulator (NAM), was developed to support this endeavor. [11C]13 was synthesized via the O-[11C]methylation of phenol 24 with a high molar activity of 212 ± 76 GBq/μmol (n = 5) and excellent radiochemical purity (>99%). PET imaging of [11C]13 in rats demonstrated its superior brain heterogeneity and reduced accumulation with pretreatment of mGluR2 NAMs, VU6001966 (9) and MNI-137 (26), the extent of which revealed a time-dependent drug effect of the blocking agents. In a nonhuman primate, [11C]13 selectively accumulated in mGluR2-rich regions and resulted in high-contrast brain images. Therefore, [11C]13 is a potential candidate for translational PET imaging of the mGluR2 function.

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Hegde, Pooja V. ; Aragaw, Wassihun W. ; Cole, Malcolm S. , et al. DOI: PubMed ID:

Abstract: Tuberculosis (TB) remains a leading cause of infectious disease-related mortality and morbidity. Pyrazinamide (PZA) is a critical component of the first-line TB treatment regimen because of its sterilizing activity against non-replicating Mycobacterium tuberculosis (Mtb), but its mechanism of action has remained enigmatic. PZA is a prodrug converted by pyrazinamidase encoded by pncA within Mtb to the active moiety, pyrazinoic acid (POA) and PZA resistance is caused by loss-of-function mutations to pyrazinamidase. We have recently shown that POA induces targeted protein degradation of the enzyme PanD, a crucial component of the CoA biosynthetic pathway essential in Mtb. Based on the newly identified mechanism of action of POA, along with the crystal structure of PanD bound to POA, we designed several POA analogs using structure for interpretation to improve potency and overcome PZA resistance. We prepared and tested ring and carboxylic acid bioisosteres as well as 3, 5, 6 substitutions on the ring to study the structure activity relationships of the POA scaffold. All the analogs were evaluated for their whole cell antimycobacterial activity, and a few representative mols. were evaluated for their binding affinity, towards PanD, through isothermal titration calorimetry. We report that analogs with ring and carboxylic acid bioisosteres did not significantly enhance the antimicrobial activity, whereas the alkylamino-group substitutions at the 3 and 5 position of POA were found to be up to 5 to 10-fold more potent than POA. Further development and mechanistic anal. of these analogs may lead to a next generation POA analog for treating TB.

Keywords: Tuberculosis ; Pyrazinoic acid ; pyrazinamide

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Product Details of [ 5720-05-8 ]

CAS No. :5720-05-8 MDL No. :MFCD00039138
Formula : C7H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BIWQNIMLAISTBV-UHFFFAOYSA-N
M.W : 135.96 Pubchem ID :79799
Synonyms :
p-Tolylboronic acid

Calculated chemistry of [ 5720-05-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.23
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : -0.33
Log Po/w (MLOGP) : 0.61
Log Po/w (SILICOS-IT) : -0.3
Consensus Log Po/w : 0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.1 mg/ml ; 0.0155 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.15 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.64
Solubility : 3.09 mg/ml ; 0.0227 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 5720-05-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5720-05-8 ]

* 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 [ 5720-05-8 ]
  • Downstream synthetic route of [ 5720-05-8 ]

[ 5720-05-8 ] Synthesis Path-Upstream   1~40

  • 1
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  • [ 1159187-59-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 157 - 169
  • 2
  • [ 110580-44-4 ]
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  • [ 31230-17-8 ]
  • [ 1159187-59-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 157 - 169
  • 3
  • [ 5720-05-8 ]
  • [ 31230-17-8 ]
  • [ 1159187-59-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 157 - 169
  • 4
  • [ 5720-05-8 ]
  • [ 4385-62-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 780 - 789
[2] Patent: CN104262238, 2016, B,
  • 5
  • [ 585-70-6 ]
  • [ 5720-05-8 ]
  • [ 52938-98-4 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 25, p. 4225 - 4229
  • 6
  • [ 5720-05-8 ]
  • [ 29886-62-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 780 - 789
[2] Patent: CN104262238, 2016, B,
  • 7
  • [ 5720-05-8 ]
  • [ 120-92-3 ]
  • [ 1671-77-8 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 16, p. 5347 - 5351
  • 8
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  • [ 106-44-5 ]
  • [ 446-65-1 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: at 40℃; Inert atmosphere; Sealed tube
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 23℃; for 2 h;
2, 2, 2-Trifluoro-l-(p-tolyl)ethanol and 1, 1, 1, 4, 4, 4-hexafluoro-3-(p-tolyl)butan-2-ol [0146] Procedure E: / Tolylboronic acid (136 mg, 1 mmol) was added to a 20 mL Biotage microwave vial equipped with a stir bar. The vial was sealed and purged with argon three times. The diazo stock solution (8 mL, 0.5 M) was added, and the reaction was stirred at 40 °C overnight. The solvent was evaporated from the crude reaction mixture under reduced pressure, and the solid was redissolved in THF (5 mL), then treated with a solution of 2 N NaOH (6 M)/30percent H2O2 (2: 1 v/v, 2 mL) at 0 °C. The reaction mixture was allowed to warm to RT and stirred for 2 h. The phases were separated, and the aqueous phase was extracted with Et20 (2 X 5 mL). The organic phases were combined, dried (MgSC^), concentrated, and purified by column chromatography to obtain 2,2,2-trifluoro-l-(p-tolyl)ethanol (43 mg, 40percent) and 1, 1, 1,4,4,4- hexafluoro-3-(p-tolyl)butan-2-ol (40 mg, 21percent) along with / methylphenol (38 mg, 14percent).
Reference: [1] Patent: WO2014/126990, 2014, A1, . Location in patent: Paragraph 0146
  • 9
  • [ 106-37-6 ]
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  • [ 149104-90-5 ]
  • [ 613-33-2 ]
  • [ 50670-49-0 ]
  • [ 5731-01-1 ]
  • [ 787-69-9 ]
  • [ 5748-38-9 ]
Reference: [1] Organometallics, 2014, vol. 33, # 12, p. 3108 - 3118
  • 10
  • [ 5720-05-8 ]
  • [ 2567-29-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4407 - 4424
[2] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
  • 11
  • [ 2042-37-7 ]
  • [ 5720-05-8 ]
  • [ 64113-85-5 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene Example 2
165 mmol of bromobenzonitrile, 247 mmol of 4-methylphenylboronic acid, 330 mmol of potassium carbonate are heated with 0.2 mol percent of trans-di-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 300 ml of xylene for 16 hours at 130° C.
The reaction solution is distilled after aqueous workup.
Yield: 94percent of 2-cyano-4-methylbiphenyl.
Reference: [1] Patent: US5559277, 1996, A,
  • 12
  • [ 873-32-5 ]
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  • [ 64113-85-5 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene Example 7
157 mmol of 2-chlorobenzonitrile, 236 mmol of 4-methylphenylboronic acid, 314 mmol of potassium carbonate are heated with 0.2 mol percent of trans-di-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 300 ml of xylene for 16 hours at 130° C.
The reaction solution is recrystallized after aqueous workup.
Yield: 73percent of 2-cyano-4-methylbiphenyl.
Reference: [1] Patent: US5559277, 1996, A,
  • 13
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  • [ 64113-85-5 ]
YieldReaction ConditionsOperation in experiment
80% With sodium carbonate In methanol; water; toluene Example 2
2M Sodium carbonate solution (200 ml) was added to a stirred mixture of 4-methylphenylboronic acid (30 g), 2-bromobenzonitrile (36.4 g), palladium (II) chloride (0.4 g), methanol (200 ml) and toluene (200 ml) at 5°C.
The temperature rose to approximately 20°C and a solid precipitated.
The reaction mixture was then heated at reflux for 2 hours.
The reaction mixture was allowed to cool and water (100 ml) was added, followed by diatomaceous earth (5 g).
The mixture was stirred for 15 minutes, then filtered through diatomaceous earth.
The organic phase of the filtrate was separated and washed with 2M sodium carbonate solution and then water.
The organic phase was then filtered and the filtrate evaporated.
The resultant solid was recrystallized from petroleum ether (b.p. 110-120°C) to give 4--methylbiphenyl-2-carbonitrile (in 80percent yield) identical to that obtained in Example 1.
Reference: [1] Patent: EP470795, 1992, A1,
  • 14
  • [ 14221-01-3 ]
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  • [ 497-19-8 ]
  • [ 64113-85-5 ]
Reference: [1] Patent: EP470795, 1992, A1,
  • 15
  • [ 7732-18-5 ]
  • [ 108-88-3 ]
  • [ 73183-34-3 ]
  • [ 17933-03-8 ]
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Reference: [1] Organic Letters, 2017, vol. 19, # 4, p. 886 - 889
  • 16
  • [ 108-88-3 ]
  • [ 73183-34-3 ]
  • [ 17933-03-8 ]
  • [ 5720-05-8 ]
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
  • 17
  • [ 108-88-3 ]
  • [ 17933-03-8 ]
  • [ 5720-05-8 ]
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
  • 18
  • [ 5720-05-8 ]
  • [ 68162-47-0 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 13, p. 2085 - 2088
[2] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 19
  • [ 128-08-5 ]
  • [ 5720-05-8 ]
  • [ 68162-47-0 ]
Reference: [1] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 20
  • [ 5720-05-8 ]
  • [ 4334-88-7 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 52, p. 6886 - 6889
[2] Chemistry - A European Journal, 2015, vol. 21, # 45, p. 16083 - 16090
[3] Inorganic Chemistry, 2017, vol. 56, # 16, p. 9765 - 9771
  • 21
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  • [ 7697-37-2 ]
  • [ 80500-27-2 ]
Reference: [1] Journal of the American Chemical Society, 1932, vol. 54, p. 4415 - 4424
[2] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 22
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  • [ 80500-27-2 ]
Reference: [1] Journal of the American Chemical Society, 1932, vol. 54, p. 4415,4418
  • 23
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  • [ 85107-55-7 ]
Reference: [1] Journal of Chemical Research, 2014, vol. 38, # 12, p. 719 - 721
  • 24
  • [ 5720-05-8 ]
  • [ 124750-53-4 ]
Reference: [1] Patent: WO2013/78237, 2013, A1,
[2] Journal of Chemical Sciences, 2014, vol. 126, # 1, p. 205 - 212
[3] Journal of Chemical Sciences, 2014, vol. 126, # 1, p. 205 - 212
  • 25
  • [ 5720-05-8 ]
  • [ 114772-40-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 897 - 906
  • 26
  • [ 21190-87-4 ]
  • [ 5720-05-8 ]
  • [ 86696-72-2 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 2 h; irradiated in a microwave
Stage #2: With hydrogenchloride In water
A mixture of 6-bromo- pyridine-2-carboxylic acid (202 mg, 1 mmol), 4-methylphenylboronic acid ( 163 mg, 1.2 mmol), and Pd(PPh3)4 (25 mg) in saturated aq. NaHC03 solution (3 mL) and DME (3 mL) was irradiated in a microwave on a Biotage Smith Synthesizer at 100 °C for 2 hrs. TLC showed the reaction was completed. The mixture was filtered and washed with water (2 x 50 mL) and ether (2 x 50 mL). The organic and aqueous layers were separated. The pH of the aqueous portion was adjusted to about 1 with 1 N aq. HCI solution. The aqueous layer was then extracted with ethyl acetate (3 x 60 mL). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated to give the title compound ( 191 mg, 90percent yield).
90%
Stage #1: With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 2 h; Microwave
Stage #2: With hydrogenchloride In water
Step A.
6-p-Tolyl-pyridine-2-carboxylic acid.
A mixture of 6-bromo-pyridine-2-carboxylic acid (202 mg, 1 mmol), 4-methylphenylboronic acid (163 mg, 1.2 mmol), and Pd(PPh3)4 (25 mg) in saturated aq. NaHCO3 solution (3 mL) and DME (3 mL) was irradiated in a microwave on a Biotage Smith Synthesizer at 100° C. for 2 hrs. TLC showed the reaction was completed.
The mixture was filtered and washed with water (2*50 mL) and ether (2*50 mL).
The organic and aqueous layers were separated.
The pH of the aqueous portion was adjusted to about 1 with 1 N aq. HCl solution.
The aqueous layer was then extracted with ethyl acetate (3*60 mL).
The combined organic layer was dried over anhydrous sodium sulfate and filtered.
The solvent was evaporated to give the title compound (191 mg, 90percent yield).
Reference: [1] Patent: WO2011/94890, 2011, A1, . Location in patent: Page/Page column 122
[2] Patent: US2012/4198, 2012, A1, . Location in patent: Page/Page column 33-34
  • 27
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  • [ 4423-09-0 ]
  • [ 5720-05-8 ]
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YieldReaction ConditionsOperation in experiment
76% With sodium carbonate In pyridine; water; toluene To a mixture of 4-tolylboronic acid (38 g, 0.28 mol), 3-bromopyridine (44 g, 0.28 mol), Na2CO3 (200 g) in toluene (500 ml) and water (500 ml) was added Pd(PPh3)4 (16 g, 0.014 mol), and refluxed for 16 h.
The reaction mixture was cooled, and the separated organic layer was washed with water and brine, and dried.
The solvent was removed to give 4-(3-pyidyl)toluene s (42 g, 90percent).
To a mixture of 4-(3-pyridyl)toluene (35 g, 0.207 mol) in pyridine (400 ml) and water (400 ml) was added KMnO4 (163 g, 1.03 mol) in portions and refiuxed for 12 h.
The reaction mixture was filtered through celite and acidified with cone. HCl.
The product was washed with water and dried to give 4-(3pyridyl)benzoic acid (32 g, 76percent) as a white solid.
Reference: [1] Patent: US2003/212012, 2003, A1,
  • 28
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Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 780 - 789
  • 29
  • [ 5720-05-8 ]
  • [ 138500-85-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
[2] Patent: WO2017/8743, 2017, A1,
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6324 - 6328[4] Angew. Chem., 2018, vol. 130, p. 6432 - 6436,5
[5] Patent: US6335451, 2002, B1,
  • 30
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  • [ 138500-85-3 ]
Reference: [1] Patent: CN107417714, 2017, A,
  • 31
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  • [ 99768-12-4 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17500 - 17521
  • 32
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  • [ 142-71-2 ]
  • [ 285983-48-4 ]
YieldReaction ConditionsOperation in experiment
50% With pyridine In dichloromethane Example 2
Synthesis of 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-urea:
The title compound was prepared as described in the final step of Example 1 from 1-(5-tert-butyl-2H-pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-urea (0.022 g, 0.050 mmol), and p-tolylboronic acid (0.014 g, 0.1 mmol), using copper (II) acetate (0.014 g, 0.075 mmol), pyridine (0.01 mL, 0.1 mmol), molecular sieves (4 Å activated, 0.030 g) and methylene chloride (2 mL).
The title compound was obtained as a yellow-white solid (0.013 g, 50percent), mp 144 -146° C; 1H NMR (DMSO) 1.26(s, 9H), 2.36(s, 3H), 2.53(t, 4H) 2.82(t, 2H), 3.52(t, 4H), 4.23(t, 2H), 6.32(s, 1H), 6.94(d, 1H), 7.33(d, 1H), 7.42(d, 1H), 7.54(m, 3H), 7.90(d, 1H), 8.15(d, 1H), 8.18(d, 1H) 8.82(s, 1H), 8.96(s, 1H); MS (CI) 528(M++H).
Reference: [1] Patent: US2002/123631, 2002, A1,
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  • [ 285983-48-4 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 34, p. 4547 - 4551
  • 34
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  • [ 405520-68-5 ]
Reference: [1] Patent: WO2004/22529, 2004, A2,
  • 35
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  • [ 380430-55-7 ]
Reference: [1] Journal of Chemical Research, 2014, vol. 38, # 12, p. 719 - 721
  • 36
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  • [ 677010-20-7 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 5, p. 1452 - 1454
  • 37
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  • [ 503536-74-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4500 - 4505
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4724 - 4729
  • 38
  • [ 13534-97-9 ]
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  • [ 170850-45-0 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 23, p. 8436 - 8439
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
  • 39
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  • [ 170850-45-0 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432
  • 40
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  • [ 170850-45-0 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 45, p. 9272 - 9277
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