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[ CAS No. 62-23-7 ] {[proInfo.proName]}

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Tian, Gui-Long ; Hsieh, Chia-Ju ; Taylor, Michelle , et al. DOI: PubMed ID:

Abstract: The difference in the secondary binding site (SBS) between the dopamine 2 receptor (D2R) and dopamine 3 receptor (D3R) has been used in the design of compounds displaying selectivity for the D3R versus D2R. In the current study, a series of bitopic ligands based on Fallypride were prepared with various secondary binding fragments (SBFs) as a means of improving the selectivity of this benzamide analog for D3R versus D2R. We observed that compounds having a small alkyl group with a heteroatom led to an improvement in D3R versus D2R selectivity. Increasing the steric bulk in the SBF increase the distance between the pyrrolidine N and Asp110, thereby reducing D3R affinity. The best-in-series compound was (2S,4R)-trans-27 which had a modest selectivity for D3R versus D2R and a high potency in the β-arrestin competition assay which provides a measure of the ability of the compound to compete with endogenous dopamine for binding to the D3R. The results of this study identified factors one should consider when designing bitopic ligands based on Fallypride displaying an improved affinity for D3R versus D2R.

Keywords: Dopamine 2 receptor ; Dopamine 3 receptor ; Fallypride ; Bitopic ligands ; PET imaging

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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. DOI: PubMed ID:

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 62-23-7 ]

CAS No. :62-23-7 MDL No. :MFCD00007352
Formula : C7H5NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :OTLNPYWUJOZPPA-UHFFFAOYSA-N
M.W : 167.12 Pubchem ID :6108
Synonyms :

Calculated chemistry of [ 62-23-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.22
TPSA : 83.12 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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.88
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : -0.93
Consensus Log Po/w : 0.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.3
Solubility : 0.828 mg/ml ; 0.00496 mol/l
Class : Soluble
Log S (Ali) : -3.26
Solubility : 0.0923 mg/ml ; 0.000552 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.15
Solubility : 12.0 mg/ml ; 0.0716 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 62-23-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P201-P202-P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338-P308+P313-P332+P313-P337+P313-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H341-H351-H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 62-23-7 ]

* 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 [ 62-23-7 ]
  • Downstream synthetic route of [ 62-23-7 ]

[ 62-23-7 ] Synthesis Path-Upstream   1~43

  • 1
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  • [ 56-81-5 ]
  • [ 62-23-7 ]
  • [ 10349-57-2 ]
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[3] Huaxue Xuebao, 1956, vol. 22, p. 134[4] Chem.Abstr., 1958, p. 7179
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  • [ 100-13-0 ]
  • [ 99-81-0 ]
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  • 12
  • [ 62-23-7 ]
  • [ 51207-86-4 ]
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  • 13
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  • [ 62-23-7 ]
  • [ 21091-98-5 ]
YieldReaction ConditionsOperation in experiment
95% With ethylene dichloride hydrochloride; benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 20℃; for 12 h; Step 1: (4-Methyl-piperazin-l-yl)-( -nitro-phenyl)-methanoneTo a solution of 4-nitro-benzoic acid (10 g, 0.0598 mol) in DMF (300 mL) 1- methyl-piperazine (7.19 g, 0.0718 mol), HOBt (10.5 g, 0.0777 mol), EDC-HCl (17.12 g, 0.0897 mol) and TEA (12.1 g, 0.1 196 mol) were added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3 x 200 mL). The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound [14 g, 95percent]; LC-MS (ESI): Calculated mass: 249.1; Observed mass: 250.0 [M+H]+ (RT: 0.10 min).
80% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; To a solution of 4-nitrobenzoicacid (1.0 g, 5.98 mmol), 1-methylpiperazine (0.599 g, 5.98 mmol) and DIPEA (2.320 g,17.95 mmol) in DMF (10 mL) was added HATU (4.55 g, 11.97 mmol). The reaction wasstirred overnight at room temperature. The mixture was quenched with water andextracted with a mix solvent of DCM and MeOH (10:1, 20 mL×3). The combinedextracts were dried over Na2SO4, filtered and concentrated. The crude was purified bycolumn chromatography on silica gel (DCM: MeOH= 20:1) to give the title compound 3a(1.2 g, 80 percent yield). LCMS: 250.1 [M+H]+.
59% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; Step: 3A-lSynthesis of (4-Methyl-piperazin-l-yl)-(4-nitro-phenyl)-methanone. Procedure:To a solution of 4-Nitro-benzoic acid (500mg, 2.9918mmol) in THF was added EDCI (856mg, 4.4865mmol), followed by HOBt (200mg, 2.9918mmol), DIPEA (1.5ml,8.9754mmol) and 1 -Methyl -piperazine (329mg, 3.291mmol) at 0°C. The resultant was stirred overnight. The reaction was monitored by the TLC (10percent methanol: chloroform).The reaction mixture was extracted with ethyl acetate and washed with water. The organic layer was concentrated and dried over Na2S04 to afford 440mg (59percent yield) of (4- Methy 1-piperazin- 1 -yl)-(4-nitro-phenyl)-methanone.
Reference: [1] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 79
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 9, p. 1615 - 1620
[3] Patent: WO2012/59932, 2012, A1, . Location in patent: Page/Page column 120-121
[4] Patent: WO2010/71885, 2010, A1, . Location in patent: Page/Page column 461
[5] Patent: US2012/277220, 2012, A1, . Location in patent: Page/Page column 15
  • 14
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  • [ 59-46-1 ]
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  • 15
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Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 41, p. 6065 - 6068
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