Np mrd loader

Showing NP-Card for 4-(2-Aminoethyl)morpholine (NP0002634)

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Record Information
Version2.0
Created at2020-11-23 18:25:43 UTC
Updated at2021-08-12 19:51:42 UTC
NP-MRD IDNP0002634
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-(2-Aminoethyl)morpholine
Provided ByBMRBBMRB logo
Description2-Morpholinoethylamine belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. 4-(2-Aminoethyl)morpholine was first documented in 2014 (PMID: 32481811). Based on a literature review very few articles have been published on 2-Morpholinoethylamine (PMID: 31155827) (PMID: 27131068).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002634 (4-(2-Aminoethyl)morpholine)


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.1644   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3356    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9144   -1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9144    1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472   -1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509   -1.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952   -1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952    1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509    1.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  2 13  1  0
  3 14  1  1
  3 15  1  0
  5 16  1  1
  5 17  1  0
  6 18  1  6
  6 19  1  0
  8 20  1  1
  8 21  1  0
  9 22  1  6
  9 23  1  0
M  END
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3D MOL for NP0002634 (4-(2-Aminoethyl)morpholine)

NP0002634
     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    3.5270    0.3390   -0.0809 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.2433    0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    0.7242    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    0.1648    0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737    1.1060    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296    0.5547    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296   -0.6134   -0.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.5548    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763   -1.1495    0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6100    0.3150   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5445    1.3318    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3103   -0.5863    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -1.1089   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    1.6057    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1112    1.1319   -0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087    1.7619   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    1.7904    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    1.2895   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0889    0.3977    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -2.5451   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -1.5500    1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108   -1.9206    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0498   -1.2407   -1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

3D SDF for NP0002634 (4-(2-Aminoethyl)morpholine)


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    4.1644   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3356    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9144   -1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9144    1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472   -1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509   -1.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952   -1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9952    1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509    1.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  2 13  1  0
  3 14  1  1
  3 15  1  0
  5 16  1  1
  5 17  1  0
  6 18  1  6
  6 19  1  0
  8 20  1  1
  8 21  1  0
  9 22  1  6
  9 23  1  0
M  END
> <DATABASE_ID>
NP0002634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCN1CCOCC1

> <INCHI_IDENTIFIER>
InChI=1S/C6H14N2O/c7-1-2-8-3-5-9-6-4-8/h1-7H2

> <INCHI_KEY>
RWIVICVCHVMHMU-UHFFFAOYSA-N

> <FORMULA>
C6H14N2O

> <MOLECULAR_WEIGHT>
130.1882

> <EXACT_MASS>
130.11061308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.862402490844705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(morpholin-4-yl)ethan-1-amine

> <ALOGPS_LOGP>
-0.99

> <JCHEM_LOGP>
-0.8253147946666672

> <ALOGPS_LOGS>
0.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.37456504066845

> <JCHEM_POLAR_SURFACE_AREA>
38.489999999999995

> <JCHEM_REFRACTIVITY>
37.0124

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.84e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-aminoethylmorpholine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0002634 (4-(2-Aminoethyl)morpholine)

NP0002634
     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    3.5270    0.3390   -0.0809 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.2433    0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    0.7242    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    0.1648    0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737    1.1060    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296    0.5547    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296   -0.6134   -0.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -1.5548    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763   -1.1495    0.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6100    0.3150   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5445    1.3318    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3103   -0.5863    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -1.1089   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    1.6057    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1112    1.1319   -0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087    1.7619   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    1.7904    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    1.2895   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0889    0.3977    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -2.5451   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -1.5500    1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108   -1.9206    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0498   -1.2407   -1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
M  END
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PDB for NP0002634 (4-(2-Aminoethyl)morpholine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0002634 (4-(2-Aminoethyl)morpholine)

COMPND    NP0002634
HETATM    1  N1  UNL     1       3.527   0.339  -0.081  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.269  -0.243   0.344  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.116   0.724   0.133  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.140   0.165   0.548  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.174   1.106   0.329  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.530   0.555   0.076  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.530  -0.613  -0.678  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.815  -1.555   0.079  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.376  -1.149   0.017  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.610   0.315  -1.121  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.545   1.332   0.216  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.310  -0.586   1.395  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.081  -1.109  -0.342  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.337   1.606   0.801  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.111   1.132  -0.896  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.909   1.762  -0.551  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.225   1.790   1.201  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.152   1.289  -0.503  1.00  0.00           H  
HETATM   19  H10 UNL     1      -3.089   0.398   1.032  1.00  0.00           H  
HETATM   20  H11 UNL     1      -1.946  -2.545  -0.355  1.00  0.00           H  
HETATM   21  H12 UNL     1      -2.181  -1.550   1.145  1.00  0.00           H  
HETATM   22  H13 UNL     1       0.211  -1.921   0.569  1.00  0.00           H  
HETATM   23  H14 UNL     1      -0.050  -1.241  -1.048  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5    9
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8
CONECT    8    9   20   21
CONECT    9   22   23
END
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SMILES for NP0002634 (4-(2-Aminoethyl)morpholine)

NCCN1CCOCC1
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INCHI for NP0002634 (4-(2-Aminoethyl)morpholine)

InChI=1S/C6H14N2O/c7-1-2-8-3-5-9-6-4-8/h1-7H2
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Synonyms
ValueSource
2-MorpholinoethanamineChEMBL
Chemical FormulaC6H14N2O
Average Mass130.1882 Da
Monoisotopic Mass130.11061 Da
IUPAC Name2-(morpholin-4-yl)ethan-1-amine
Traditional NameN-aminoethylmorpholine
CAS Registry NumberNot Available
SMILES
NCCN1CCOCC1
InChI Identifier
InChI=1S/C6H14N2O/c7-1-2-8-3-5-9-6-4-8/h1-7H2
InChI KeyRWIVICVCHVMHMU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
Substituents
  • Morpholine
  • Tertiary amine
  • Tertiary aliphatic amine
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.99ALOGPS
logP-0.83ChemAxon
logS0.88ALOGPS
pKa (Strongest Basic)9.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.49 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.01 m³·mol⁻¹ChemAxon
Polarizability14.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB03096
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID361265
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tehrani MB, Rezaei Z, Asadi M, Behnammanesh H, Nadri H, Afsharirad F, Moradi A, Larijani B, Mohammadi-Khanaposhtani M, Mahdavi M: Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-carboxamide-N-morpholine Hybrids as New Anti-Alzheimer Agents. Chem Biodivers. 2019 Jul;16(7):e1900144. doi: 10.1002/cbdv.201900144. Epub 2019 Jun 26. [PubMed:31155827 ]
  2. Pires Gouvea D, Vasconcellos FA, Dos Anjos Berwaldt G, Neto AC, Fischer G, Sakata RP, Almeida WP, Cunico W: 2-Aryl-3-(2-morpholinoethyl)thiazolidin-4-ones: Synthesis, anti-inflammatory in vivo, cytotoxicity in vitro and molecular docking studies. Eur J Med Chem. 2016 Aug 8;118:259-65. doi: 10.1016/j.ejmech.2016.04.028. Epub 2016 Apr 20. [PubMed:27131068 ]
  3. Zhu H, Fan J, Zhang S, Cao J, Song K, Ge D, Dong H, Wang J, Peng X: Ratiometric fluorescence imaging of lysosomal Zn(2+) release under oxidative stress in neural stem cells. Biomater Sci. 2014 Jan 29;2(1):89-97. doi: 10.1039/c3bm60186b. Epub 2013 Sep 11. [PubMed:32481811 ]