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Chemical Structure| 57184-23-3 Chemical Structure| 57184-23-3

Structure of 57184-23-3

Chemical Structure| 57184-23-3

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Product Details of [ 57184-23-3 ]

CAS No. :57184-23-3
Formula : C11H22N2
M.W : 182.31
SMILES Code : N1(CC2CCCCC2)CCNCC1
MDL No. :MFCD01075237
InChI Key :LRPGNFROBDUREU-UHFFFAOYSA-N
Pubchem ID :2735885

Safety of [ 57184-23-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 57184-23-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 64.29
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

15.27 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.77
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.98
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.71
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.81
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.11
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.88

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.09
Solubility 1.5 mg/ml ; 0.00821 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.93
Solubility 2.16 mg/ml ; 0.0118 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.22
Solubility 1.1 mg/ml ; 0.00605 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.01 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.76

Application In Synthesis of [ 57184-23-3 ]

* 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 [ 57184-23-3 ]

[ 57184-23-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 22117-85-7 ]
  • [ 57184-23-3 ]
  • [ 102535-29-5 ]
  • 2
  • [ 412293-89-1 ]
  • [ 57184-23-3 ]
  • 3
  • [ 57184-23-3 ]
  • [ 130288-93-6 ]
  • [ 134346-48-8 ]
  • 4
  • [ 57184-23-3 ]
  • [ 130288-93-6 ]
  • 4-(cyclohexylmethyl)-N-[3-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7yloxy)propyl]-1-piperazinecarboxamide [ No CAS ]
  • 5
  • [ 57184-23-3 ]
  • [ 94193-55-2 ]
  • 7-[4-(4-Cyclohexylmethyl-piperazin-1-yl)-4-oxo-butoxy]-1,5-dihydro-imidazo[2,1-b]quinazolin-2-one [ No CAS ]
  • 6
  • [ 57184-23-3 ]
  • [ 10191-60-3 ]
  • C14H24N4S [ No CAS ]
  • 7
  • [ 872408-08-7 ]
  • [ 57184-23-3 ]
  • 2-(4-cyclohexylmethyl-piperazin-1-yl)-<i>N</i>-(1,3-dibromo-6-oxo-5,6-dihydro-4<i>H</i>-cyclopenta[<i>c</i>]thiophen-4-yl)-acetamide [ No CAS ]
  • 8
  • [ 512784-08-6 ]
  • [ 57184-23-3 ]
  • 5-(4-cyclohexylmethyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid 3-trifluoromethyl-benzylamide [ No CAS ]
  • 9
  • [ 512784-04-2 ]
  • [ 57184-23-3 ]
  • 5-(4-cyclohexylmethyl-piperazin-1-yl)-5-oxo-2-[2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-styryl-azetidin-1-yl]-pentanoic acid 3-trifluoromethyl-benzylamide [ No CAS ]
  • 10
  • [ 7483-61-6 ]
  • [ 57184-23-3 ]
  • C54H68N4O12 [ No CAS ]
  • 11
  • [ 105396-63-2 ]
  • [ 57184-23-3 ]
  • C54H68N4O13 [ No CAS ]
  • 12
  • [ 884647-32-9 ]
  • [ 57184-23-3 ]
  • C21H27ClN4S [ No CAS ]
  • 13
  • [ 57184-23-3 ]
  • 1-(5-amino-4H-1,2,4-triazol-3-yl)-4-(cyclohexylmethyl)piperazine [ No CAS ]
  • 14
  • [ 2550-36-9 ]
  • [ 57184-23-3 ]
  • 15
  • (2R)-1-[3,5-bis(trifluormethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-[4-azido-2-butin-1-yl]piperazine [ No CAS ]
  • [ 57184-23-3 ]
  • C38H46F6N8O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 70℃; for 6h; Die nachfolgenden Verbindungen der Beispiele 8 bis 65 wurden nach einem automatisierten Herstellungsverfahren hergestellt.Hierzu wurde pro Ansatz eine Lösung von 0,03 mmol (2R)-1-[3,5- Bis(trifluormethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(4-azido-2-butin-1-yl)piperazin der Formel IV (Herstellung siehe Beispiel 1/Syntheseweg 1B)) in 1 ml Ethylacetat jeweils mit einer Lösung von 0,03 mmol des als Reaktionspartner vorgesehenen sekundären Amins der Formel V in 1 ml Ethylacetat umgesetzt und anschließend mit 3 ml Ethylacetat verdünnt. Auf das Reaktionsgemische wurde Stickstoffgas gegeben und es wurde jeweils 6 Stunden lang bei 70 C gerührt. Der Reaktionsendpunkt wurde Dünnschicht-chromatographisch bestimmt. Nach vollendeter Umsetzung wurden die einzelnen Reaktionsgemische jeweils im Vakuum zur Trockene eingedampft. Aus dem Rückstand wurde ohne weitere Aufreinigung jeweils eine Probe für die Hochleistungs-Flüssigkeitschromatographie (= HPLC) und für die automatische Massenspektroskopie zur Bestimmung der Reinheit bzw. zur Strukturbestätigung entnommen.
  • 16
  • [ 73568-25-9 ]
  • [ 57184-23-3 ]
  • 2-(4-cyclohexylmethyl-piperazin-1-yl)-quinoline-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 110℃; for 4.83h; Example 39; Synthesis of (3,5-bis-trifluoromethyl-benzyl)- [2-(4-cyclohexylmethyI-piperazin-l-yl)- quinolin-3-ylmethyl]-carbamic acid ethyl ester; Step (i): Synthesis of 2-(4-cyclohexylmethyl-piperazin-l-yl)-quinoline-3-carbaldehyde; l-(Cyclohexylmethyl)piperazine (0.42 niL, 2.2 mmol) was added to a mixture of 2-chloro-3-quinolinecarboxaldehyde (0.383 g, 2.0 mmol) and potassium carbonate (0.7 g, 5.0 mmol) in anhydrous DMF (4 mL) at ambient temperature under a nitrogen atmosphere. After being stirred for 20 minutes, the reaction mixture was heated at 110 C for 4.5 h. After cooling to room temperature this mixture was diluted with water (40 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were EPO <DP n="205"/>washed with brine, dried over sodium sulfate, filtered, and then concentrated under vacuum to give a pale brown crude product. Purification by silica gel column chromatography and eluting with 2.5% methanol in dichloromethane afforded the title compound (0.56 g), yield: 86%.Mp 95-96 C;1H NMR (CDCl3, 300 MHz): δ 10.17 (s, IH), 8.48 (s, IH), 7.81 (t, J= 8.2 Hz, 2H), 7.67(m, IH), 7.36 (m, IH), 3.51 (t, J= 5.1 Hz, 4H), 2.61 (t, J= 4.8 Hz, 4H), 2.22 (d, J= 7.2Hz, 2H), 1.84-1.68 (m, 6H), 1.31-1.13 (m, 3H), 0.96-0.82 (m, 2H).777/z MS: 338 (M++., 100%)
  • 17
  • [ 548766-96-7 ]
  • [ 57184-23-3 ]
  • [ 549510-85-2 ]
YieldReaction ConditionsOperation in experiment
93% 4-Cyclohexylmethyl-piperazine-1-carboxylic acid 4-(4-trifluoromethyl-phenoxy)-phenyl Ester The hydrochloride of the title compound was prepared from 4-(4-trifluoromethyl-phenoxy)-phenyl chloroformate and 1-cyclohexylmethyl-piperazine, yield 93%. White crystals, m.p. 256-258 C.; IR (KBr): ν 1715 (C=O) cm-1.
  • 18
  • [ 548767-06-2 ]
  • [ 57184-23-3 ]
  • [ 549510-86-3 ]
YieldReaction ConditionsOperation in experiment
76% 4-Cyclohexylmethyl-piperazine-1-carboxylic Acid 4-(3-chloro-5-trifluoromethyl-pyridin-2-yloxy)-phenyl Ester The hydrochloride of the title compound was prepared from 4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)-phenyl chloroformate and 1-cyclohexylmethyl-piperazine, yield 76%. White crystals, m.p. 265-266 C.; IR (KBr): ν 1732 (C=O) cm-1.
  • 19
  • [ 57184-23-3 ]
  • [ 130288-93-6 ]
  • hydrated dihydrochloride salt [ No CAS ]
  • 1-(Cyclohexylmethyl)-4-[4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-1-oxybutyl]piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.75 g (100%) EXAMPLE 22 1-(Cyclohexylmethyl)-4-[4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yloxy)-1-oxybutyl]piperazine STR39 Reaction of N-(cyclohexylmethyl)piperazine and 4-[(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)oxy]butyric acid (2 g) analogously to the procedure of Example 4 gave the title compound after crystallization from methanol/diethyl ether as the hydrated dihydrochloride salt; yield 3.75 g (100%), m.p. 258-260 C. (dec). Anal. Calcd. for C25 H33 N5 O3.2HCl.0.4 H2 O: C, 56.48; H, 6.79: N, 13.18; H2 O, 1.36. Found: C, 56.72: H, 7.47; N, 12.47; H20, 0.35%. 1 H-NMR (DMSO-d6) delta 0.93 (2H, q, J=11 Hz), 1.15 (3H, m), 1.50 to 1.95 (6H, m), 2.01 (2H, t, J=6 Hz), 2.58 (2H, m), 2.90 to 3.20 (4H, m), 3.33 (1H, t, J=12 Hz), 3.44 (2H, bs), 3.77 (1H, t, J=12 Hz), 4.08 (3H, t, J=6 Hz), 4.39 (1H, d, J=12 Hz), 7.24 (1H, dd, J=9 Hz, J1 =2.5 Hz), 7.44 (1H, dd, J=2.5 Hz), 7.72 (1H, s), 7.84 (1H, d, J=9 Hz), 11.13 (1H, bs), 11.50 (2H, bs).
  • 20
  • [ 145798-60-3 ]
  • [ 57184-23-3 ]
  • 1-[3-(4-cyclohexanemethyl-1-piperazinyl)-propyl]-2(1H)-quinolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N-methyl-acetamide; dichloromethane; Example 1 1-[3-(4-Cyclohexanemethyl-1-piperazinyl)-propyl]-2(1H)-quinolinone 1-(3-Bromopropyl)-2(1H)-quinolinone (250 mg) obtained in Preparation example 1, cyclohexanemethylpiperazine (171 mg), and potassium carbonate (195 mg) were suspended in dimethylformamide (3 ml). The suspension was heated at 80C for 10 hr. Dichloromethane was added to the reaction solution. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under the reduced pressure to give an oil. The oil was purified by column chromatography on silica gel to give the title compound (272 mg). 1H NMR (CDCl3) δ (ppm): 0.80 - 0.98 (2H, m), 1.09 - 1.30 (3H, m), 1.42 - 1.55 (1H, m), 1.61 - 1.80 (5H, m), 1.93 (2H, tt, J = 7.7 and 7.2 Hz), 2.13 (2H, d, J = 7.2 Hz), 2.36 - 2.58 (8H, m), 2.48 (2H, t, J = 7.2 Hz), 4.35 (2H, t, J = 7.7 Hz), 6.69 (1H, d, J = 9.5 Hz), 7.18- 7.24 (1H, m), 7.50 - 7.58 (3H, m), 7.66 (1H, d, J = 9.5 Hz). Mass spectrum EIMS, m/z 367 (M+).
  • 21
  • [ 1141923-52-5 ]
  • [ 57184-23-3 ]
  • C33H43N5O4 [ No CAS ]
  • 22
  • [ 111631-72-2 ]
  • [ 57184-23-3 ]
  • [ 1218949-66-6 ]
  • 23
  • [ 1220889-22-4 ]
  • [ 57184-23-3 ]
  • [ 1220889-19-9 ]
  • 24
  • [ 1220889-23-5 ]
  • [ 57184-23-3 ]
  • [ 1220889-21-3 ]
  • 25
  • [ 7755-92-2 ]
  • [ 2550-36-9 ]
  • [ 57184-23-3 ]
  • 26
  • [ 57184-23-3 ]
  • [ 91047-79-9 ]
  • [ 1254211-04-5 ]
  • 27
  • [ 54006-63-2 ]
  • [ 57184-23-3 ]
  • [ 1277167-61-9 ]
  • 30
  • [ 57184-23-3 ]
  • [ 62-46-4 ]
  • 1-(4-cyclohexylmethylpiperazin-1-yl)-5-(1,2-dithiolan-3-yl)pentan-1-one hydrochloride [ No CAS ]
  • 31
  • [ 50-00-0 ]
  • [ 7559-81-1 ]
  • [ 57184-23-3 ]
  • [ 1428245-55-9 ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; General procedure: The basic substituent was introduced in the 6th-position of chlorokojic acid via a Mannich-type reaction, using formaline and an appropriate substituted piperidine or piperazine derivatives in methanol at room temperature. The reaction proceeded very rapidly. Mannich bases were prepared by the reaction of substituted piperazine or piperidine derivatives and chlorokojic acid in MeOH with 37% formaline. The mixture was stirred vigorously for 15-25min at room temperature. The resulting precipitate was collected by filtration and washed with cold MeOH. Formation of the desired new Mannich base derivatives were confirmed on the basis of elemental analysis, and the structures of the compounds were supported by spectral data. Chlorokojic acid; Yield 60%, mp: 166-167C. 6-(Chloromethyl)-3-hydroxy-2-((4-(4-iodophenyl)piperazin-1-yl)methyl)-4H-pyran-4-one (Compound 9) C17H18ClIN2O3, yield: 56%; mp: 182-3C; %CHN Found (Calculated): C 44.65 (44.32), H 3.91 (3.94), N 6.61 (6.08); IR ν (cm-1): 1630 (C=O), 1456 (C=C), 1202 (C-O); 1H NMR (DMSO-d6, 400MHz) δ ppm: 2.60 (4H; t; J=4.8; piperazine-H2′, H6′), 3.13 (4H; t; J=4.8; piperazine-H3′,H5′), 3.62 (2H; s; -CH2-), 4.66 (2H; s; ClCH2-), 6.55 (1H; s; H5), 6.76 (2H; d; J=9.2; Ar-H2″, H6″), 7.46 (2H; d; J=9.2; Ar-H3″, H5″), 9.22 (1H; s; -OH); 13C NMR (DMSO, 400MHz) δ ppm: 42.11, 48.35, 52.77, 54.02, 81.32, 113.12, 118.49, 137.93, 144.82, 148.14, 151.19, 161.93, 174.15; ESI-MS (m/z): 399 (100%), 461 (M++H), 463 (M++H+2), 483 (M++Na). Ethyl 4-((6-(chloromethyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)methyl)piperazine-1-carboxylate (Compound 24) C14H19ClN2O5, yield: 63%; mp: 136-7C; %CHN Found (Calculated): C 50.59 (50.84), H 5.63 (5.79), N 8.38 (8.47); IR ν (cm-1): 1679 (C=O), 1424 (C=C), 1220 (C-O); 1H NMR (DMSO-d6, 400MHz) δ ppm: 1.67 (3H; t; J=7.0; -CH3), 2.44 (4H; t; J=5.2; piperazine-H2′, H6′), 3.36 (4H; t; J=5.2; piperazine-H3′,H5′), 3.60 (2H; s; -CH2-), 4.02 (2H; q; J=6.8; -CH2CH3), 4.65 (2H; s; ClCH2-), 6.55 (1H; s; H5), 9.19 (1H; br s; -OH); 13C NMR (DMSO, 400MHz) δ ppm: 15.22, 42.10, 43.93, 52.62, 53.10, 61.39, 113.12, 144.86, 147.90, 155.23, 161.94, 174.16; ESI-MS (m/z): 331 (M++H), 333 (M++H+2), 353 (M++Na, 100%). Benzyl 4-((6-(chloromethyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)methyl)piperazine-1-carboxylate (Compound 25) C19H21ClN2O5, yield: 64%; mp: 141-2C; %CHN Found (Calculated): C 57.86 (58.09), H 5.25 (5.39), N 7.07 (7.13); IR ν (cm-1): 1679 (C=O), 1446 (C=C), 1225 (C-O); 1H NMR (DMSO-d6, 400MHz) δ ppm: 2.45 (4H; t; J=4.8; piperazine-H2′,H6′), 3.40 (4H; m; piperazine-H3′,H5′), 3.60 (2H; s; -CH2-), 4.65 (2H; s; ClCH2-), 5.07 (2H; s; -CH2COO-), 6.55 (1H; s; H5), 7.28-7.38 (5H; m; Ar-H), 9.20 (1H; br s; -OH); 13C NMR (DMSO, 400MHz) δ ppm: 42.10, 44.15, 52.64, 54.01, 66.89, 113.12, 128.20, 128.50, 129.09, 137.57, 144.82, 148.05, 155.05, 161.92, 174.17; ESI-MS (m/z): 393 (M++H), 395 (M++H+2), 415 (M++Na, 100%). 1-((6-(Chloromethyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)methyl)-4-phenylpiperidine-4-carbonitrile (Compound 26) C19H19ClN2O3, yield: 71%; mp: 156-7C; %CHN Found (Calculated): C 64.35 (63.60), H 5.39 (5.34), N 7.91 (7.81); IR ν (cm-1): 1660 (C=O), 1455 (C=C), 1200 (C-O); 1H NMR (DMSO-d6, 400MHz) δ ppm: 1.99-2.56 (8H; m; piperidine); 3.68 (2H; s; -CH2-), 4.66 (2H; s; ClCH2-), 6.56 (1H; s; H5), 7.34-7.54 (5H; m; Ar-H); 9.24 (1H; br s; -OH); 13C NMR (DMSO, 400MHz) δ ppm: 36.15, 42.09, 42.29, 50.69, 54.03, 113.19, 122.67, 126.33, 128.75, 129.71, 140.82, 144.87, 148.19, 161.95, 174.19; ESI-MS (m/z): 381 (100%, M++Na), 359 (M++H), 361 (M++H+2). 6-(Chloromethyl)-3-hydroxy-2-((4-phenyl-5,6-dihydropyridin-1(2H)-yl)methyl)-4H-pyran-4-one (Compound 27) C18H18ClNO3, yield: 76%; mp: 165-6C; %CHN Found (Calculated): C 64.67 (65.16), H 5.33 (5.47), N 4.16 (4.22); IR ν (cm-1): 1622 (C=O), 1456 (C=C), 1198 (C-O); 1H NMR (DMSO-d6, 400MHz) δ ppm: 2.49-3.19 (6H; m; pyridine), 3.69 (2H; s; -CH2-), 4.67 (2H; s; ClCH2-), 6.14 (1H; t; J=3.6; pyridine), 6.55 (1H; s; H5), 7.22-7.42 (5H; m; Ar-H); 13C NMR (DMSO, 400MHz) δ ppm: 27.99, 42.13, 50.20, 52.76, 53.62, 113.13, 122.47, 125.24, 127.69, 129.04, 134.55, 140.75, 144.76, 148.52, 161.94, 174.18; ESI-MS (m/z): 332 (100%, M++H), 334 (M++H+2), 354 (M++Na). 6-(Chloromethyl)-2-((4-(4-chlorophenyl)-5,6-dihydropyridin-1(2H)-yl)methyl)-3-hydroxy-4H-pyran-4-one (Compound 28) C18H17Cl2NO3, yield: 97%; mp: 166-7C; %CHN Found (Calculated): C 59.15 (59.03), H 4.61 (4.68), N 4.01 (3.82); IR ν (cm-1): 1631 (C=O), 1458 (C=C), 1194 (C-O); 1H NMR (DMSO-d6, 400MHz) δ ppm: 2.47-3.27 (6H; m; pyridine), 3.69 (2H; s; -CH2-), 4.66 (2H; s; ClCH2-), 6.18 (1H; br s; pyridine), 6.55 (1H; s; H5), 7.36 (2H; d; J=8.4; Ar-H2″, H6″), 7.44 (2H; d; J=8.4; Ar-H3″, H5″); 13C NMR (DMSO, 400MHz) δ ppm: 27.86, 42.13, 50.08, 52.70, 53.55, 113.13, 123.38, 127.02, 128.92, 132.19, 133.46, 139.54, 144.76, 148.47, 161.94, 174.17; ESI-MS (m/z): 218 (100%), 366 (M++H), 368 (M++H+2), 388 (M++Na). 6-(Chloromethyl)-2-((4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl)methyl)-3-hydroxy-4H-...
  • 32
  • 3-(3,6-dichloro-9H-carbazol-9-yl)propyl methanesulfonate [ No CAS ]
  • [ 57184-23-3 ]
  • 3,6-dichloro-9-{3-[4-(cyclohexylmethyl)piperazin-1-yl]propyl}-9H-carbazole [ No CAS ]
  • 33
  • [ 57184-23-3 ]
  • [ 2984-50-1 ]
  • [ 1584124-77-5 ]
  • 34
  • 4-((1-crboxypentyl)oxy)-2-hydroxy-5-((4-(phenoxymethyl)phenyl)ethynyl)benzoic acid [ No CAS ]
  • [ 57184-23-3 ]
  • C39H46N2O6 [ No CAS ]
  • 35
  • [ 57184-23-3 ]
  • [ 10199-89-0 ]
  • 4-[4-(cyclohexylmethyl)piperazin-1-yl]-7-nitro-2,1,3-benzoxadiazole [ No CAS ]
 

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