MED CHEM2 (Huigens)-MOD 02

name this drug[image]
Largazole
[image]list all func groups!
[image]
name this drug[image]

Linezolid

purely synthetic 

[oxazolidenone antibacterial]

[image]name this drug
Ciprofloxacin
[image]name this drug
Tipranavir
[image]name this drug
erythromycin
[image]name this drug
Gefitinib
[image]name this drug
Sorafenib
[image]Name this drug
Quinine
[image]name this drug
Cephalexin
[image]name this drug
Penicillin G
This pharmacophore represents what class of drugs[image]
Penicillins & derivatives
name this drug[image]
tetracycline

name the functional groups on this drug?

WHat drug is this anyway?

[image]

CIPROFLOXACIN

[image]

name this drug 

[image]

Lipitor (atorvastatin)

This Pharmacophore represents which drug class?

[image]

STATINS!

Name this compound

[image]

Ageliferin (marine sponge derivative)

name this drug

[image]

Lovastatin

Magnesium Bromide (MgBr) is used as what type of reagent?

 

Grignard Reagent

List in order of least to most reactive aka most to least stable

>>>

Amide, Aldehyde, Carboxylic Acid, Ester, Ketone

1.Carboxylic Acid

2. Amide

3. Ester

4. Ketone

5. Aldehyde

Which Compound is found in many drugs?(most stable)

 

 

A. Amide

B. Aldehyde

C. Carboxylic Acid

D. Ester

E.Ketone

F. All of them

C. Carboxylic Acid

Aromatic, Non-Aromatic, or ANti-Aromatic

[image]

Aromatic

Aromatic, Non-Aromatic, or ANti-Aromatic

[image]

Aromatic
Aromatic, Non-Aromatic, or ANti-Aromatic[image]
Aromatic

Aromatic, Non-Aromatic, or ANti-Aromatic

 

[image]

Anti-aromatic

Aromatic, Non-Aromatic, or ANti-Aromatic

 

[image]

Non aromatic

 

Aromatic, Non-Aromatic, or ANti-Aromatic

[image]

Non aromatic

Which of thes best describes Ciprofloxacins indication/function?

A. ANti-fungal

B. Anti-anginal

C. ANti-malarial

D. Anti-biotic

E. Anti-bacterial

E. Anti-bacterial

 

Anti bacterials are totally synthetic

Anti Biotics are nature derived

Name this compound

[image]

Morphine

Name this compound

[image]

Oxycodone

name this compound

[image]

Hydrocodone

Name this compound

[image]

Codeine

name this drug

[image]

Heroin

This structure is the pharmacophore for 40% of antibiotics. It is termed________

 

[image]

Beta-Lactam

Irreversible Inhibition is characterized by what types of bonds?

(ex: ionic,hydrogen bonds….etc)

Covalent Bonds

The process by which a quinoline is converted to a quinolone is known as __________.

 

ex: [image]

Tautomerization

Name this functional group

[image]

Carbamate

Name this functional group

[image]

Toluene

Name this functional group

[image]

Aniline

Name this functional group

[image]

Nitrile

Name this functional group

[image]

Nitrosamine

Name this functional group

[image]

Alkene/Olefin

Name this functional group

[image]

Quinoline

Name this functional group

[image]

Quinolone

Name this functional group

[image]

pyridine

name this functional group

[image]

Thioester

Name this Functional Group

[image]

Nitrosos group

This image depicts a carbapenem.

[image]

They are produced by

A. Bacteria

B. Fungi 

C. Humans

D. Fumigation

A. Bacteria

Amines that are part of a conjugated system or with an adjacent electron withdrawing group are often___hybridized?

 

A. sp

B. sp2

C. sp1

D. sp3

B. sp2
Erythromycin demonstrates selective targeting for bacterial______
Ribosomes
Solubility, Absorption, Interaction with biological target, metabolism, excretion describe______properties of functional groups.
Physicochemical

This drug is called ________.

It acts as a topoisomerase inhibitor.

[image]

TOPOTECAN
Topotecan is a anticancer agent. It works as a ______________ inhibitor.

topoisomerase

[image]

TRUE or FALSE.

 

Penicillins as well as statins come from fungi.

TRUE

Name this 

[image]

imidazole

name this structure

[image]

Pyrrole

 

Name this structure

[image]

Furan
[image]Name this structure
Thiophene

Name this structure

[image]

Indole

Name this structure

 

[image]

Benzofuran

Name this structure 

[image]

Benzothiophene
Taxol is an anti cancer agent and targets____
Microtubules (freezes/stabilizes)
Quinine is an anti malaria agent and targets

Tat2p-mediated tryptophan transport and causes tryptophan starvation

Statins target
HMG COA reductase (inhibitors of this enzyme)
Ciprofloxacin inhibits bacterial DNA synthesis and  targets__________
topoisomerase II (responsible for supercoiling and uncoiling of DNA)

Largazole (depicted below) comes from cyanobacteria and targets_________

[image]

Histone Deacetyleases aka HDACs

(Largazole is a Histone Deacetylase Inhibitor)

Sorafenib is a kidney cancer drug that targets_____
Tyrosine protein Kinases
Gefitinib(IRESSA) is a cancer drug that targets_______
EGFR and ERK 1/2
Tipranavir treats multi drug resisitant HIV and targets______
HIV and CAAX Prenyl Proteases (protease inhibitor)

Cephalasporin C is depicted below and targets______

[image]

Penicillin Binding Proteins PBPs(inhibits cell wall synthesis)

Name this drug

[image]

Streptomycin (it is an aminoglycoside)

Name this drug

[image]

Daptomycin (a lipopeptide antibiotic)

Name the functional group

[image]

Guanidine

Name the group

[image]

Pyrazole

Name?

[image]

oxazole

Name?

[image]

Pyrimidine

Name?

[image]

Benzimidazole

Name?

[image]

isoquinoline

Rx name?

[image]

Epothilone A

[anticancer]

Rx name?[image]
Camptothecin [anticancer]

Rx name

[image]

Halfordinol

[anti-adipogenic activity, obesity]

Rx name

[image]

ondansetron

[nausea from cancer tx]

Rx name

[image]

Rivaroxaban (aka Xarelto)

[blood thinner, irregular heart beat]

Rx name

[image]

Nexium (aka esomeprazole)

[ppi, tx for GERD]

Completely synthetic rx

Rx name

[image]

AMIAS [hypertension, heart failure]

benzimidazole prodrug

True or false

 

Carboxylic acids and Tetrazoles have similar acidities/pKa values

TRUE!!!

Replacement or modification of specific pharmacophoric (functional) groups with other groups with similar properties is_____________.

 

 

Bioisosteric Replacement

Rx name?

[image]

Tripelennamine

[1st generation antihistamine,antipruritic]

Rx name

[image]

Methaphenilene

[antihistamine, anticholinergic]

Rx name

[image]

a-tocopherol (aka Vitamin E)

[orally enhances immune system,antioxidant, topically promotes skin health]

Group name?

[image]

catechol

Rx name?

[image]

Isoproterenol

[tx for bradycardia aka slow heart rate, heart block]

Rx name

[image]

Soterenol

[bronchodilator]

Rx name

[image]

Estradiol

[female hormone hormone replacement, menopause]

Rx name (this is the trans- version, not cis-)

[image]

Diethylstilbestrol (trans)

{synthetic estrogen}

The trans and cis version are equipotent to estrogen

Acidity can be rationalized if you look at what type of organic structures?

Resonance structure

 

Phenols PKA?

 

[image]

9-11

Sulfonamide pKa (R2 is a hydrogen)?

 [image]

9-10

Imide pKa?

[image]

 

9-10

Alkylthiol pKa?

[image]

10-11

Thiophenol pKa?

[image]

9-10

N-aryl sulfonilamide pKa?

[image]

6-7

Sulfonimide pKa?

[image]

5-6

Alkylcarboxylic acid pKa?

[image]

5-6

Arylcarboxylic acid pKa?

[image]

4-5

Sulfonic Acid pKa?

[image]

0-1

Rx name?

[image]

Irinotecan

[cancer Tx]

Topoisomerase 1 inhibitor

Rx name

 

[image]

Cefaclor (Ceclor)

2nd generation cephalasporin antibiotic

Water solubility is largely dependent on the # of _______’s

you are able to solubilize. They are accounted for by certain functional groups.

Carbon’s

Compound name 

 

[image]

Salicylic acid

[Monohydroxybenzoic acid derivative]

This molecule may have trouble with dissolution due to _______________________.

[image]

INTRAmolecular hydrogen bonding

[of the carboxylic acid and alcohol] 

 

[image]

Rx name?

 

[image]

NOVOCAINE

[local anesthetic]

Based on pi values a molecule with a log p of 0.3 is _____

while a molecule with a pi value of 0.9 is ________

 

Soluble, insoluble (respectively)

 

 

Log p must be less than 0.5 for a molecule to be considered soluble in water. A molecule must have a Log p of less than 5 to have oral bioavailability. 

Rx  name

 

[image]

Ibuprofen

[NSAID]

Rx name

[image]

Captopril (Capoten)

[ACE inhibitor,hypertension]

Rx name

[image]

Nadolol (Corgard)

 

[beta blocker, hypertension]

Rx top selling drug of 2014

 

[image]

Synthroid (Levothyroxine)

 

[Thyroid hormone replacement]

T4 hormone produced naturally in our bodies

 

Rx name

 

[image]

Zoloft

[selective serotonin reuptake inhibitor (AKA antidepressant)]

purely synthetic

Name functional group

 

[image]

Napthalene

Structural group? (HINT: 4)

 

[image]

tetrahydronaphthalene

Functional group?

 

[image]

Piperizine

 

[It is a core functional group seen in LATUDA]

Rx name?

 

[image]

LATUDA (Lurasidone)

 

[antipschotic, bipolar depression]

Rx?

 

[image]

Testosterone

[T deficiency]

Rx?

 

[image]

esterone

[estrogenic hormone secreted by the ovary as well as adipose tissue ]

Rx?

 

[image]

progesterone

[endogenous steroid and progestogen sex hormone]

Rx?

 

[image]

norethynodrel

 

[synthetic progestational hormone with actions and uses similar to those of PROGESTERONE]

Rx?

 

[image]

mestranol

[synthetic steroidal estrogen]

Rx?

 

[image]

Cortisone

 

[steroid, antiinflammatory]

 

NATURAL PRODUCT

Rx?

 

[image]

Cortisol

 

[steroid hormone]

NATURAL PRODUCT

Rx?

 

[image]

PREDNISONE

[synthetic steroid analog, ANTI INFLAMMATORY]

Rx name?

 

[image]

Methicillin

 [?-lactam antibiotic of the penicillin class]

In med chem we see in reversible reactions/equations that equilibrium lies with the more ________ species.

 

BASIC

Rx?

 

[image]

Prostglandin

 

[lipids involved in injury and illness]

pH =
pH = -log [H+]
pOH =
pOH = -log[-OH]
[H+] =

[H+] = 10= 10-pH

 

[-OH] = 10= 10-pOH
[-OH] = 10= 10-pOH
ALcohols hydrogen bond to water which can _______the water solubility
Increase
Water solubility as described in the monofunctional model says the average functional group can account for about ___carbons
6
Water solubility as described in the polyfunctional model says the average functional group can account for about ___carbons
3

Molecule is?

[image]

Cytosine

[one of four main bases of DNA]

pKa =

pKa = pH +log ([acid]/[base])

 

pKa = pH +log ([acid]/[base])

Rx name?

 

[image]

Amobarbital

 

[sedative barbiturate, tranquilizer]

Rx name?

 

[image]

Cetirizine (Zyrtec)

[antihistamine]

Rx?

[image]

Phenylpropanolamine

[stimulant, decongestant, and anorectic]

rx name?

[image]

crestor (rosuvastatin)

[hyperlipidemia]

synthetic derivative

 

Rx?

 

[image]

Methadone

[Morphine Derivative]

opiod analgesic/treats pain or opiate withdrawals

WHat is the name of the two methyl groups up top?

[image]

Gem-dimethyl

Remember this position!!!!

 

[image]

[image]
x

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