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[ CAS No. 271-63-6 ] {[proInfo.proName]}

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Chemical Structure| 271-63-6
Chemical Structure| 271-63-6
Structure of 271-63-6 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations      Expand+

David A Vargas ; Xinkun Ren ; Arkajyoti Sengupta , et al. DOI: PubMed ID:

Abstract: Catalysis with engineered has provided more efficient routes for the production of active pharmaceutical agents. However, the potential of biocatalysis to assist in early-stage drug discovery campaigns remains largely untapped. In this study, we have developed a biocatalytic strategy for the construction of sp3-rich polycyclic compounds via the intramolecular cyclopropanation of and related heterocycles. Two carbene transferases with complementary regioisomer selectivity were evolved to catalyse the stereoselective cyclization of benzothiophene substrates bearing diazo ester groups at the C2 or C3 position of the heterocycle. The detailed mechanisms of these reactions were elucidated by a combination of crystallographic and computational analyses. Leveraging these insights, the substrate scope of one of the biocatalysts could be expanded to include previously unreactive substrates, highlighting the value of integrating evolutionary and rational strategies to develop for new-to-nature transformations. The molecular scaffolds accessed here feature a combination of three-dimensional and stereochemical complexity with 'rule-of-three' properties, which should make them highly valuable for fragment-based drug discovery campaigns.

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Abdelkader, Elwy H. ; Qianzhu, Haocheng ; Huber, Thomas , et al. DOI: PubMed ID:

Abstract: Genetic encoding of a noncanonical amino acid (ncAA) in an in vivo expression system requires an aminoacyl-tRNA synthetase that specifically recognizes the ncAA, while the ncAA must not be recognized by the canonical protein expression machinery. We succeeded in genetically encoding 7-aza-tryptophan (7AW), which is isoelectronic with tryptophan. The system is fully orthogonal to protein expression in E. coli, enabling high-yielding site-selective isotope-labeling in vivo. 7AW is readily synthesized from serine and 7-aza-indole using a tryptophan synthetase β-subunit (TrpB) mutant, affording easy access to isotope-labeled 7AW. Using labeled 7AW produced from 15N/13C-labeled serine, we produced 7AW mutants of the 25 kDa Zika virus NS2B-NS3 protease. 15N-HSQC spectra display single cross-peaks at chem. shifts near those observed for the wild-type protein labeled with 15N/13C-tryptophan, confirming the structural integrity of the protein and yielding straightforward NMR resonance assignments for site-specific probing.

Keywords: 7-azatryptophan ; genetic encoding ; isoelectronicsubstitution ; NMR spectroscopy ; selective isotopelabeling

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Shriver, James A. ; Kaller, Kaylie S. ; Kinsey, Ally L. , et al. DOI: PubMed ID:

Abstract: The spontaneous conversion of 3-indoxyl to indigo was a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids.

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Product Details of [ 271-63-6 ]

CAS No. :271-63-6 MDL No. :MFCD00005606
Formula : C7H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :MVXVYAKCVDQRLW-UHFFFAOYSA-N
M.W : 118.14 Pubchem ID :9222
Synonyms :
Chemical Name :1H-Pyrrolo[2,3-b]pyridine

Calculated chemistry of [ 271-63-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.09
TPSA : 28.68 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 1.31
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 0.86 mg/ml ; 0.00728 mol/l
Class : Soluble
Log S (Ali) : -1.51
Solubility : 3.63 mg/ml ; 0.0307 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.163 mg/ml ; 0.00138 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 271-63-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 271-63-6 ]

* 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.

  • Upstream synthesis route of [ 271-63-6 ]
  • Downstream synthetic route of [ 271-63-6 ]

[ 271-63-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 271-63-6 ]
  • [ 882562-39-2 ]
Reference： [1] Patent: WO2013/6634, 2013, A2,
[2] Patent: WO2013/70606, 2013, A1,
[3] Patent: WO2014/74471, 2014, A1,
[4] Patent: WO2014/201332, 2014, A1,
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