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[ CAS No. 123855-51-6 ] {[proInfo.proName]}

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Chemical Structure| 123855-51-6
Chemical Structure| 123855-51-6
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Berg, Kaja ; Hegde, Pooja ; Pujari, Venugopal , et al. DOI: PubMed ID:

Abstract: The electron transport chain (ETC) in the cell membrane consists of a series of redox complexes that transfer electrons from electron donors to acceptors and couples this electron transfer with the transfer of protons (H+) across a membrane. This process generates proton motive force which is used to produce ATP and a myriad of other functions and is essential for the long-term survival of Mycobacterium tuberculosis (Mtb), the causative organism of tuberculosis (TB), under the hypoxic conditions present within infected granulomas. Menaquinone (MK), an important carrier molecule within the mycobacterial ETC, is synthesized de novo by a cluster of enzymes known as the classic/canonical MK biosynthetic pathway. MenA (1,4-dihydroxy-2-naphthoate prenyltransferase), the antepenultimate enzyme in this pathway, is a verified target for TB therapy. In this study, we explored structure-activity relationships of a previously discovered MenA inhibitor scaffold, seeking to improve potency and drug disposition properties. Focusing our campaign upon three molecular regions, we identified two novel inhibitors with potent activity against MenA and Mtb (IC50 = 13-22 μM, GIC50 = 8-10 μM). These analogs also displayed substantially improved pharmacokinetic parameters and potent synergy with other ETC-targeting agents, achieving nearly complete sterilization of Mtb in combination therapy within two weeks in vivo. These new inhibitors of MK biosynthesis present a promising new strategy to curb the continued spread of TB.

Keywords: 1,4-dihydroxy-2-naphthoate prenyltransferase ; MenA ; MenA inhibitors ; Menaquinone ; Mtb ; Mycobacterium tuberculosis ; Piperidine derivatives ; SAR

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 25952-53-8 ; ; ; ; ; ; 22246-18-0 ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 123855-51-6 ]

CAS No. :123855-51-6 MDL No. :MFCD02094488
Formula : C11H21NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :CTEDVGRUGMPBHE-UHFFFAOYSA-N
M.W : 215.29 Pubchem ID :2764081
Synonyms :
Chemical Name :tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Calculated chemistry of [ 123855-51-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.56
TPSA : 49.77 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.66
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 1.24
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.93
Consensus Log Po/w : 1.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.65
Solubility : 4.84 mg/ml ; 0.0225 mol/l
Class : Very soluble
Log S (Ali) : -1.81
Solubility : 3.33 mg/ml ; 0.0155 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.11
Solubility : 16.7 mg/ml ; 0.0774 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 123855-51-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 123855-51-6 ]

* 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 [ 123855-51-6 ]

[ 123855-51-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 67247-13-6 ]
  • [ 123855-51-6 ]
  • [ 776296-04-9 ]
  • 2
  • [ 1137475-57-0 ]
  • [ 123855-51-6 ]
  • [ 1137476-28-8 ]
YieldReaction ConditionsOperation in experiment
62% N-Boc-4-piperidinemethanol (860 mg, 4.0 mmol) was added to a suspension of 60% sodium hydride (160 mg, 4.0 mmol) in DMF (40 mmol) at room temperature. After 20 minutes, <strong>[1137475-57-0]2-bromo-4-chloro-5-nitropyridine</strong> (949 mg, 4.0 mmol) was added in one portion, and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with ether and washed with water. The aqueous phase was extracted with ether. The combined organic phases were washed with water and brine, then dried (Na2SO4) and concentrated. Silica column chromatography, eluting with 20% ethyl acetate - hexane, gave tert-butyl 4-((2-bromo-5-nitropyridin-4-yloxy)methyl)piperidine-1-carboxylate (789 mg, 62%) as a viscous, pale yellow oil which solidified on standing.1H NMR (CDCI3, 400MHz) delta 8.80 (s, 1H), 7.20 (s, 1H)7 4.05-4.15 (m, 2H), 4.00 (d, 2H, J = 6.3 Hz), 2.75-2.85 (m, 2H), 2.10 (m, 1H), 1.80-1.90 (m, 2H), 1.45 (s, 9H), 1.20-1.30 (m, 2H). LCMS (1 ) Rt = 2.45 min; m/z (ESI+) 316, 318 (MH+),
  • 3
  • [ 123855-51-6 ]
  • [ 1023595-19-8 ]
  • 4
  • [ 1354961-13-9 ]
  • [ 123855-51-6 ]
  • tert-butyl 4-((4-(tert-butoxycarbonyl)-2-chloro-5-fluorophenoxy)-methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium tert-butylate; In dimethyl sulfoxide; at 20℃; for 1h; Potassium tert-butoxide (6.2 g, 55.6 mmol) was added to a solution of tert-butyl 4-(hydroxymethyl) piperidine-1-carboxylate (10.0 g, 46.3 mmol) and tert-butyl 5-chloro-2, 4-difluorobenzoate (12.6 g, 50.9 mmol) in DMSO (200 mL) . After stirring at room temperature for1h, the reaction mixture was diluted with water (500 mL) and extracted with EtOAc (200 mL × 3) . The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate, from 20/1 to 5/1) to afford the target compound (12.3 g, yield: 60) as a pale yellowliquid. LCMS (ESI) m/z: 331.9. [M-111]+.
60% With potassium tert-butylate; In dimethyl sulfoxide; at 20℃; for 1h;Inert atmosphere; Step 1 (0232) Potassium tert-butoxide (6.2 g, 55.6 mmol) was added to a solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (10.0 g, 46.3 mmol) and <strong>[1354961-13-9]tert-butyl 5-chloro-2,4-difluorobenzoate</strong> (12.6 g, 50.9 mmol) in DMSO (200 mL). After stirring at room temperature for 1 h, the reaction mixture was diluted with water (500 mL) and extracted with EtOAc (200 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate, from 20/1 to 5/1) to afford the target compound (12.3 g, yield: 60%) as a pale yellow liquid. LCMS (ESI) m/z: 331.9. [M-111]+.
  • 5
  • [ 123855-51-6 ]
  • [ 581060-27-7 ]
  • 6
  • [ 123855-51-6 ]
  • [ 183170-69-6 ]
  • 7
  • [ 13589-72-5 ]
  • [ 123855-51-6 ]
  • tert-butyl 4-((4-chloro-2-cyanophenoxy)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
17 g With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 24h; 15 g of <strong>[13589-72-5]5-chloro-2-hydroxybenzonitrile</strong> was added to 180 ml of tetrahydrofuran, and 19 g of tert-butyl 4- (hydroxymethyl) piperidine-1-carboxylate, 42 g of triphenylphosphine, 35 g of bis Isopropyl acetate, stirred at room temperature for 24 hours, concentrated and the residue was chromatographed on a silica gel column to obtain 17 g of tert-butyl 4 - ((4-chloro-2-cyanophenoxy) methyl) piperidine-1-carboxylate.
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 0 - 35℃; for 12h; To a solution of <strong>[13589-72-5]5-chloro-2-hydroxybenzonitrile</strong> (2.50 g), tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate(3.50 g) and triphenylphosphine (5.12 g) in THF (50 mL) was added 1.9 M DIAD (toluene solution, 10.3 mL) at 0C, andthe reaction mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated, and the residuewas purified by silica gel column chromatography (ethyl acetate/hexane) to give tert-butyl 4-((4-chloro-2-cyanophenoxy)methyl)piperidine-1-carboxylate as a crude product.
  • 8
  • [ 52764-11-1 ]
  • [ 123855-51-6 ]
  • tert-butyl 4-(((2,6-dichloropyridin-3-yl)oxy)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 0 - 35℃; for 8h; To a solution of <strong>[52764-11-1]2,6-dichloropyridin-3-ol</strong> (1.06 g), tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (1.39 g)and triphenylphosphine (2.03 g) in THF (30 mL) was added 1.9 M DIAD (toluene solution, 4.08 mL) at 0C, and thereaction mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated, and the residue waspurified by silica gel column chromatography (ethyl acetate/hexane) to give tert-butyl 4-(((2,6-dichloropyridin-3-yl)oxy)methyl)piperidine-1-carboxylate as a crude product
  • 9
  • [ 123855-51-6 ]
  • [ 597563-39-8 ]
  • 10
  • [ 32315-10-9 ]
  • [ 145742-50-3 ]
  • [ 123855-51-6 ]
  • tert-butyl 4-[(2-chloro-4-formyl-5-methoxyphenyl)carbamoyloxymethyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% <strong>[145742-50-3]4-amino-5-chloro-2-methoxybenzaldehyde</strong> (3a) (6.9 g, 37.2 mmol) was dissolved in toluene (100 ml), to which triphosgene (5.51 g, 18.6 mmol) was added, followed by a reaction at 120C for 2 hours, and the resultant was concentrated to obtain Reaction solution 1. Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (2a) (2.00 g, 9.29 mmol) was dissolved in tetrahydrofuran (50 ml), to which Reaction solution 1 and then triethylamine (3.76 g, 37.2 mmol) were added, followed by a reaction at 70C for 2 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether (v/v) = 1:9 to 3:7) to give yellow oily tert-butyl 4-[(2-chloro-4-formyl-5-methoxy-phenyl)carbamoyloxymethyl]piperidine-1-carboxyl ate (3b) (2.2 g, yield: 74%). 1H NMR (400 MHz, CDCl3) delta 10.29 (s, 1H), 8.05 (s, 1H), 7.83 (s, 1H), 7.41 (s, 1H), 4.16 (d, 2H), 4.09 (d, 2H), 3.95 (s, 3H), 2.73 (m, 2H), 1.96 - 1.83 (m, 1H), 1.75 (d, 2H), 1.46 (s, 9H), 1.32 - 1.18 (m, 2H). LCMS m/z =449.3 [M+23].
  • 11
  • [ 123855-51-6 ]
  • [ 4983-28-2 ]
  • [ 1314391-51-9 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere; General procedure: Compound 3-(dimethylamino)propan-1-ol (825.28 mg, 8 mmol) and triphenylphosphine (2.517 g, 9.6mmol) were added successively to a suspension of 19 (1.044 g, 8 mmol) in THF (15 mL) under nitrogen.A solution of DIAD (1.67 g, 9.6 mmol) in THF (2 mL) was then slowly added dropwise with ice cooling.The resultant solution was stirred at room temperature for 12 hours. The aqueous phase wasextracted with dichloromethane (40 mL 3). The combined organic layer was washed with H2O (40 mL)and brine (20 mL), and then dried over anhydrous Na2SO4, filtered and evaporated in vacuo. Theresidue was purified by flash chromatography over silica gel (DCM/MeOH = 40:110:1) to give 20a.
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