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[ CAS No. 76855-69-1 ] {[proInfo.proName]}

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Chemical Structure| 76855-69-1
Chemical Structure| 76855-69-1
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Product Citations

Product Citations      Expand+

You-Chen Lin ;

Abstract: Polycyclic guanidinium alkaloids (PGAs) constitute a class of complex marine natural products exhibiting a broad range of biological activities such as antiviral, antitumoral, and antimicrobial activities; however, little information regarding their biological functions and targets is known mainly due to the low natural abundance and their challenging synthesis. Developing an efficient and modular synthetic approach towards PGAs is therefore critical to further develop these scaffolds as chemical probes. Herein, we report a novel synthesis of PGAs using bicyclic ?lactams as key intermediates. From these bicyclic ?-lactams, a short sequence of chemical transformations would allow access to PGA scaffolds and open the door to understanding their biological activity. A small library of batzelladine D and its analogs was generated, and screening of these compounds revealed the first antimicrobial evaluation of this family. The promising preliminary data suggest the potential for further development of the batzelladines for use as antimicrobal agents. In parallel, we plan to expand this synthetic approach to other PGAs such as the monanchocidin family. To this end, the progress toward the synthesis of monanchocidin A is described.(Counter ions of PGAs are omitted in this document for clarity)

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Lin, Y. C. ; Ribaucourt, A. ; Moazami, Y. , et al. DOI: PubMed ID:

Abstract: Herein, we describe a stereodivergent route to (±)-batzelladine D (2), (+)-batzelladine D (2), (?)-batzelladine D (2), and a series of stereochemical analogues and explore their antimicrobial activity for the first time. The concise synthetic approach enables access to the natural products in a sequence of 8–12 steps from readily available building blocks. Highlights of the synthetic strategy include gram-scale preparation of a late stage intermediate, pinpoint stereocontrol around the tricyclic skeleton, and a modular strategy that enables analogue generation. A key bicyclic β-lactam intermediate not only serves as the key controlling element for pyrrolidine stereochemistry but also serves as a preactivated coupling partner to install the ester side chain. The stereocontrolled synthesis allowed for the investigation of the antimicrobial activity of batzelladine D, demonstrating promising activity that is more potent for non-natural stereoisomers.

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Product Details of [ 76855-69-1 ]

CAS No. :76855-69-1 MDL No. :MFCD00077636
Formula : C13H25NO4Si Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 287.43 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 76855-69-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.85
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 79.65
TPSA : 64.63 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 2.4
Log Po/w (WLOGP) : 1.65
Log Po/w (MLOGP) : 1.54
Log Po/w (SILICOS-IT) : 0.37
Consensus Log Po/w : 1.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.525 mg/ml ; 0.00183 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.115 mg/ml ; 0.000399 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.53
Solubility : 0.856 mg/ml ; 0.00298 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.61

Safety of [ 76855-69-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:
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