SID49666180

ID: ALA1550435

Cas Number: 477861-95-3

PubChem CID: 1490541

Max Phase: Preclinical

Molecular Formula: C16H14ClN3

Molecular Weight: 283.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1CNc1ncnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C16H14ClN3/c1-11-4-2-3-5-12(11)9-18-16-14-7-6-13(17)8-15(14)19-10-20-16/h2-8,10H,9H2,1H3,(H,18,19,20)

Standard InChI Key:  WHAUTSXRLRVMIY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    1.4320    3.6424    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    3.6424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    2.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.1674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259    1.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    1.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175    2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114   -0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -0.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259   -0.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -1.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259   -1.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175   -0.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0
  2  6  1  0
  2 12  2  0
  3  7  2  0
  3 12  1  0
  4  7  1  0
  4 14  1  0
  5  6  1  0
  5  7  1  0
  5  8  2  0
  6  9  2  0
  8 11  1  0
  9 10  1  0
 10 11  2  0
 13 14  1  0
 13 15  1  0
 13 16  2  0
 15 17  2  0
 15 20  1  0
 16 18  1  0
 17 19  1  0
 18 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1550435

   7-chloro-N-[(2-methylphenyl)methyl]quinazolin-4-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 283.76

Molecular Weight (Monoisotopic): 283.0876

AlogP: 4.20

#Rotatable Bonds: 3

Polar Surface Area: 37.81

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.09

CX LogP: 4.33

CX LogD: 4.33

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.78

Np Likeness Score: -1.59

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70. Taygerly, Joshua P and 31 more authors.  2013-02-15  Discovery of INT131: a selective PPARγ modulator that enhances insulin sensitivity.  [PMID:23294830]

71. Cappelli, Andrea A and 16 more authors.  2013-05  Synthesis and structure-activity relationship studies in serotonin 5-HT(1A) receptor agonists based on fused pyrrolidone scaffolds.  [PMID:23466604]

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73. Lamotte, Yann Y and 12 more authors.  2014-02-15  Discovery of novel indazole derivatives as dual angiotensin II antagonists and partial PPARγ agonists.  [PMID:24462665]

74. Calleri, E and 10 more authors.  2014-05-26  Resveratrol and its metabolites bind to PPARs.  [PMID:24796862]

75. Gege, Christian C, Schlüter, Thomas T and Hoffmann, Thomas T.  2014-11-15  Identification of the first inverse agonist of retinoid-related orphan receptor (ROR) with dual selectivity for RORβ and RORγt.  [PMID:25305688]

76. Gangwal, Rahul P RP, Damre, Mangesh V MV, Das, Nihar R NR, Sharma, Shyam S SS and Sangamwar, Abhay T AT.  2015-01-15  Biological evaluation and structural insights for design of subtype-selective peroxisome proliferator activated receptor-α (PPAR-α) agonists.  [PMID:25491112]

77. Garcia-Vallvé, Santiago S and 7 more authors.  2015-07-23  Peroxisome Proliferator-Activated Receptor γ (PPARγ) and Ligand Choreography: Newcomers Take the Stage.  [PMID:25734377]

78. Fuhr, Luise L, Rousseau, Morten M, Plauth, Annabell A, Schroeder, Frank C FC and Sauer, Sascha S.  2015-05-22  Amorfrutins Are Natural PPARγ Agonists with Potent Anti-inflammatory Properties.  [PMID:25938459]

79. Asteian, Alice A and 16 more authors.  2015-09-10  Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists.  [PMID:26396687]

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81. Waszkielewicz, A M AM and 9 more authors.  2016-04-15  Design, physico-chemical properties and biological evaluation of some new N-[(phenoxy)alkyl]- and N-{2-[2-(phenoxy)ethoxy]ethyl}aminoalkanols as anticonvulsant agents.  [PMID:26988801]

82. Okazaki, Shogo S and 6 more authors.  2016-11-01  Structure-activity relationship studies of non-carboxylic acid peroxisome proliferator-activated receptor α/δ (PPARα/δ) dual agonists.  [PMID:27622746]

83. Pellicciari, Roberto R and 12 more authors.  2016-10-13  Discovery of 3α,7α,11β-Trihydroxy-6α-ethyl-5β-cholan-24-oic Acid (TC-100), a Novel Bile Acid as Potent and Highly Selective FXR Agonist for Enterohepatic Disorders.  [PMID:27652492]

84. Piemontese, Luca L and 13 more authors.  2017-02-15  New diphenylmethane derivatives as peroxisome proliferator-activated receptor alpha/gamma dual agonists endowed with anti-proliferative effects and mitochondrial activity.  [PMID:28076827]

85. Frkic, Rebecca L RL and 9 more authors.  2017-06-08  Structure-Activity Relationship of 2,4-Dichloro-N-(3,5-dichloro-4-(quinolin-3-yloxy)phenyl)benzenesulfonamide (INT131) Analogs for PPARγ-Targeted Antidiabetics.  [PMID:28485590]

86. Pirat, Celine C and 12 more authors.  2017-09-08  Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression.  [PMID:28609708]

87. Yu, Jinha and 12 more authors.  2017-09-14  Polypharmacology of N6-(3-Iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA) and Related A3 Adenosine Receptor Ligands: Peroxisome Proliferator Activated Receptor (PPAR) γ Partial Agonist and PPARδ Antagonist Activity Suggests Their Antidiabetic Potential.  [PMID:28799755]

88. Boubia, Benaïssa and 23 more authors.  2018-03-22  Design, Synthesis, and Evaluation of a Novel Series of Indole Sulfonamide Peroxisome Proliferator Activated Receptor (PPAR) α/γ/δ Triple Activators: Discovery of Lanifibranor, a New Antifibrotic Clinical Candidate.  [PMID:29446942]

89. Dou, Xiao-Zheng XZ, Nath, Dinesh D, Shin, Younghwa Y, Ma, Jian-Xing JX and Duerfeldt, Adam S AS.  2018-09-01  Structure-guided evolution of a 2-phenyl-4-carboxyquinoline chemotype into PPARα selective agonists: New leads for oculovascular conditions.  [PMID:29628329]

90. Del Rio, Carmen and 13 more authors.  2018-10  VCE-004.3, a cannabidiol aminoquinone derivative, prevents bleomycin-induced skin fibrosis and inflammation through PPARγ- and CB2 receptor-dependent pathways.  [PMID:30033591]

91. Laghezza, Antonio A and 11 more authors.  2018-09-27  Identification of the First PPARα/γ Dual Agonist Able To Bind to Canonical and Alternative Sites of PPARγ and To Inhibit Its Cdk5-Mediated Phosphorylation.  [PMID:30199253]

92. Li, Zheng Z and 5 more authors.  2018-11-05  Design, synthesis, and biological evaluation of novel pan agonists of FFA1, PPARγ and PPARδ.  [PMID:30296685]

93. Rycek, Lukas and 12 more authors.  2018-11-26  Stereoselective Synthesis of the Isomers of Notoincisol A: Assigment of the Absolute Configuration of this Natural Product and Biological Evaluation.  [PMID:30362739]

94. Ahn, Sungjin S and 11 more authors.  2019-02-22  Adiponectin-Secretion-Promoting Phenylethylchromones from the Agarwood of Aquilaria malaccensis.  [PMID:30672698]

95. Giampietro, Letizia L and 18 more authors.  2019-04-11  Novel Phenyldiazenyl Fibrate Analogues as PPAR α/γ/δ Pan-Agonists for the Amelioration of Metabolic Syndrome.  [PMID:30996794]

96. Ahn, Sungjin S and 11 more authors.  2019-07-01  2-Phenyl-8-(1-phenylallyl)-chromenone compounds have a pan-PPAR modulator pharmacophore.  [PMID:31128991]

97. Ling, Taotao T and 10 more authors.  2019-08-08  Mechanistic Insight on the Mode of Action of Colletoic Acid.  [PMID:31294974]

98. Yamamoto, Keisuke and 12 more authors.  2019-11-15  Development of a novel class of peroxisome proliferator-activated receptor (PPAR) gamma ligands as an anticancer agent with a unique binding mode based on a non-thiazolidinedione scaffold.  [PMID:31623970]

99. Passeri, Daniela and 6 more authors.  2019-08-01  Dissecting the allosteric FXR modulation: a chemical biology approach using guggulsterone as a chemical tool.  [PMID:31673308]

100. Dowarah, Jayanta and Singh, Ved Prakash.  2020-03-01  Anti-diabetic drugs recent approaches and advancements.  [PMID:32008883]

101. Peiretti, Franck and 11 more authors.  2020-11-12  A Novel N-Substituted Valine Derivative with Unique Peroxisome Proliferator-Activated Receptor γ Binding Properties and Biological Activities.  [PMID:33142057]

102. An, Seungchan and 20 more authors.  2020-12-24  Discovery and Structure-Activity Relationships of Novel Template, Truncated 1'-Homologated Adenosine Derivatives as Pure Dual PPARγ/δ Modulators.  [PMID:33325691]

Source

Source(1):

• PubChem BioAssays