CH 203 Betulin Project Lab. Slide presentation accompanying the project write-up

Snyder, John K.

English

Boston University Institutional Repository (OpenBU)

Boston UniversityOpenBU http://open.bu.eduChemistry The Betulin Project2014The Betulin Project Introduction2014 - Accompanying Slide Showhttps://hdl.handle.net/2144/12965Boston UniversityThe Betulin Project – Fall Semester CH 203, 2014 Boston UniversityInstructor: Prof. John K. SnyderLaboratory Fellow: Dr. Ya Zhou, PFFBetulin Group Meetings – Thursdays, 3 pmBetulin Laboratory: Alternate Fridays, 1 - ? pmBetulin: Protective Compound from White and Paper BirchH2CC C CHCH2CHOH3C CH3CH3H AOHHOHHHO HOHOBetulinic AcidHHHO HOHBetulinAnti-Melanoma – Betulinic AcidLipinski’s Rule of Five1)  No more than 5 Hydrogen Bond Donors (N-H and O-H)2)  No more than 10 Hydrogen Bond Acceptors (all N’s and O’s)3)  MW less than 5004)  cLogP = 5 or lessHOCO2HHHHBetulinic AcidMW 456.36cLogP 7.38283CO2HHHHH2N cLogP 2.74CO2HHHH3NCO2MeHHHH2N cLogP = 5.48Betulinic Acid DerivativesAnti-MelanomaHOHHH OHOHOHHHHNOCO2HCH3cLogP 4.94IC50 MEL-2: 1.5 µMIC50 KB: 4.6 µMcLogP 7.34IC50 MEL-2: 4.2 µMIC50 KB: >20 µMAnti-HIVHOHHH OHOcLogP 7.34EC50 HIV: 1.4 µMIC50 cytotox.: 13.0 µMTherapeutic Index: 9.0OHHH OcLogP 7.09EC50 HIV: 6.6 X 10-4 µMIC50 cytotox.: 14.2 µMTherapeutic Index: 21,515BetulinO OCO2HOHOOLast Year’s ProgressHOCH2OHHHHNitrogen IncorporationAcCl/py/DMAPHOCH2OAcHHH(diacetate, minor)[ox]OCH2OAcHHH1Reductive AminationsCH2OAcHHHRHNMonoacetylationOxidationX1Br2HOCH2OHHHHBrBrRNH2HOCO2RHHHBrNHR'HOCO2RHHHRNAlkene TransformationsX(messy)CH2OAcHHHHNOHONCH2OAcHHHOxime FormationBeckmann    RearrangementFive Experiments to here!Allobetulin AnaloguesFive Experiments to here!CH2OHHHHHOH2SO4. SiO2HHHHOODess-Martin PeriodinaneHHHOO Oxime FormationHHHOHON123 43Beckmann RearrangementHHHO5cLogP 4.84HNOUltimate TargetsCH2OAcHHHHNOCO2HHHHHNO1) Deacetylation2) OxidationcLogP 4.10HHHOHNOReductionHHHOHNcLogP 6.8From BetulinFrom Allobetulin

The Betulin Project Introduction 2014 - Accompanying Slide Show

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The Betulin Project Introduction 2014 - Accompanying Slide Show

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