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[ CAS No. 71989-31-6 ] {[proInfo.proName]}

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Chemical Structure| 71989-31-6
Chemical Structure| 71989-31-6
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Product Citations

Product Citations

Gardner, Eric D. ; Dimas, Dustin A. ; Finneran, Matthew C. , et al. DOI: PubMed ID:

Abstract: Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II and tubulin polymerization However, the inability to perform late-stage modification of the indole ring has limited the structure-activity relationship studies of this class of natural products. Herein, we describe an efficient chemoenzymic approach for the late-stage modification of tryprostatin B using a cyclic dipeptide N-prenyltransferase (CdpNPT) from Aspergillus fumigatus, which generates novel analogs functionalized with allylic, benzylic, heterocyclic, and diene moieties. Notably, this biocatalytic functionalizational study revealed high selectivity for the indole C6 position. Seven of the 11 structurally characterized analogs were exclusively C6-alkylated, and the remaining four contained predominant C6-regioisomers. Of the 24 accepted substrates, 10 provided >50% conversion and eight provided 20-50% conversion, with the remaining six giving <20% conversion under standard conditions. This study demonstrates that prenyltransferase-based late-stage diversification enables direct access to previously inaccessible natural product analogs.

Keywords: biocatalysts ; chemoenzymatic synthesis ; late-stage functionalization ; prenyltransferase ; tryprostatin

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Product Details of [ 71989-31-6 ]

CAS No. :71989-31-6 MDL No. :MFCD00037122
Formula : C20H19NO4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :ZPGDWQNBZYOZTI-SFHVURJKSA-N
M.W : 337.37 Pubchem ID :688135
Synonyms :

Calculated chemistry of [ 71989-31-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.3
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 96.68
TPSA : 66.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 3.36
Log Po/w (WLOGP) : 3.1
Log Po/w (MLOGP) : 2.78
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 2.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.07
Solubility : 0.0285 mg/ml ; 0.0000844 mol/l
Class : Moderately soluble
Log S (Ali) : -4.44
Solubility : 0.0122 mg/ml ; 0.0000362 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.61
Solubility : 0.00834 mg/ml ; 0.0000247 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.64

Safety of [ 71989-31-6 ]

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

Application In Synthesis of [ 71989-31-6 ]

* 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 [ 71989-31-6 ]

[ 71989-31-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 29022-11-5 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 108-24-7 ]
  • [ 198561-07-8 ]
  • Ac-Pro-Asp-Phe-Gly-OH [ No CAS ]
  • 2
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 71989-31-6 ]
  • [ 71989-26-9 ]
  • [ 198561-07-8 ]
  • NH2-Pra-Lys(Boc)-Pra-Pro-Gly-Pra-Ala-Pra-Pro-Gly-OH [ No CAS ]
  • 3
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 71989-31-6 ]
  • [ 198561-07-8 ]
  • NH2-Pra-Ala-Pra-Pro-Gly-Pra-Ala-Pra-Pro-Gly-OH [ No CAS ]
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