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[ CAS No. 73-24-5 ] {[proInfo.proName]}

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Chemical Structure| 73-24-5
Chemical Structure| 73-24-5
Structure of 73-24-5 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Zhou, Jujun ; Deng, Youchao ; Iyamu, Iredia D. , et al. DOI: PubMed ID:

Abstract: S-Adenosyl-L-methionine (SAM) analogs are adaptable tools for studying and therapeutically inhibiting SAM-dependent methyltransferases (MTases). Some MTases play significant roles in host-pathogen interactions, one of which is Clostridioides difficile-specific DNA adenine MTase (CamA). CamA is needed for efficient sporulation and alters persistence in the colon. To discover potent and selective CamA inhibitors, we explored modifications of the solvent-exposed edge of the SAM adenosine moiety. Starting from the two parental compounds (6e and 7), we designed an adenosine analog (11a) carrying a 3-phenylpropyl moiety at the adenine N6-amino group, and a 3-(cyclohexylmethyl guanidine)-Et moiety at the sulfur atom off the ribose ring. Compound 11a (IC50 = 0.15 μM) is 10x and 5x more potent against CamA than 6e and 7, resp. The structure of the CamA-DNA-inhibitor complex revealed that 11a adopts a U-shaped conformation, with the two branches folded toward each other, and the aliphatic and aromatic rings at the two ends interacting with one another. 11a occupies the entire hydrophobic surface (apparently unique to CamA) next to the adenosine binding site. Our work presents a hybrid knowledge-based and fragment-based approach to generating CamA inhibitors that would be chem. agents to examine the mechanism(s) of action and therapeutic potentials of CamA in C. difficile infection.

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Product Details of [ 73-24-5 ]

CAS No. :73-24-5 MDL No. :MFCD00041790
Formula : C5H5N5 Boiling Point : -
Linear Structure Formula :N4C5H3(NH2) InChI Key :GFFGJBXGBJISGV-UHFFFAOYSA-N
M.W : 135.13 Pubchem ID :190
Synonyms :
6-Aminopurine;Vitamin B4;NSC 14666
Chemical Name :Purin-6-amine

Calculated chemistry of [ 73-24-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 36.09
TPSA : 80.48 ?2

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) : -7.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.53
Log Po/w (XLOGP3) : -0.53
Log Po/w (WLOGP) : -0.06
Log Po/w (MLOGP) : -0.82
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : -0.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.01
Solubility : 13.2 mg/ml ; 0.0977 mol/l
Class : Very soluble
Log S (Ali) : -0.69
Solubility : 27.5 mg/ml ; 0.204 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.77
Solubility : 2.27 mg/ml ; 0.0168 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 73-24-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 73-24-5 ]

* 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 [ 73-24-5 ]

[ 73-24-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 105-36-2 ]
  • [ 73-24-5 ]
  • [ 25477-96-7 ]
Reference： [1] European Journal of Medicinal Chemistry, 2019, p. 28 - 44
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