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107 Cards in this Set

  • Front
  • Back
  • 3rd side (hint)

etomidate

ketamine

phenobarbital

5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione



5,5-, 1,5,5- 치환만 수면·항불안·마취 효능


5-, 1,3-, 1,3,5,5- 는 불활성 또는 경련유발


pH 에 따라 3개의 lactam group이 lactim으로 변화


5번 탄소 치환탄소수↑, 질소 치환기의 탄소수↑ : 지용성↑


N에 큰 알킬기는 경련유발, N1, N3모두 치환시 불활성



2-phenybutyronitrile 원료


benzyl cyanide(phenylacetonitrile) 원료


urea(thiopental 제외, barbiturate, trimethadione) 원료


diethylmalonate 아님!

zolpidem

N,N-dimethyl-2-(6-methyl-2-p-tolylimidazopyridin-3-yl)acetamide



• Mannich reaction


4-Methylphenacetyl bromide 원료


2-amino-5-methylpyridine 원료

diazepam

7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one



링A - 방향성고리 필요. 7번에 EWG 도입시 활성유지. 6,8,9번에 EWG 도입시 활성상실.


링B - 1번 치환기는 활성과 무관하지만 bulky하면 친화력↓. 2번에 proton acceptor(carbonyl,sulfinyl)필요. 3번에 hydroxyl 도입시 대사 빠르고 ester화 가능. 4,5번 이중결합 포화시 친화력↓


링C - 수용체 결합에 필요한 구조는 아님. 입체적으로 도움. 2’에 EWG 도입시 활성유지. 4’에 EWG 도입시 활성감소. 링C는 heteroaromatic, cycloalkenyl 가능.



• Friedel-Crafts acylation


2-amino-5-chloro-benzophenone 원료


• glycine ethyl ester 원료


2-Amino-5-chlorobenzoic acid 원료


• benzoyl chloride 원료

lorazepam

• (RS)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one



• 링A - 방향성고리 필요. 7번에 EWG 도입시 활성유지. 6,8,9번에 EWG 도입시 활성상실.


• 링B - 1번 치환기는 활성과 무관하지만 bulky하면 친화력↓. 2번에 proton acceptor(carbonyl,sulfinyl)필요. 3번에 hydroxyl 도입시 대사 빠르고 ester화 가능. 4,5번 이중결합 포화시 친화력↓


• 링C - 수용체 결합에 필요한 구조는 아님. 입체적으로 도움. 2’에 EWG 도입시 활성유지. 4’에 EWG 도입시 활성감소. 링C는 heteroaromatic, cycloalkenyl 가능.



2-(2-chlorobenzoyl)-4-chloroaniline 원료


diethyl-2-aminomalonate 원료

alprazolam

8-chloro-1-methyl-6-phenyl-4H-triazolobenzodiazepine



• 2-amino-5-chloro-benzophenone 원료


• glycine ethyl ester 원료


• acetylhydrazine 원

baclofen

eperisone

sulpiride

chlorpromazine

olanzapine

2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thienobenzodiazepine



dibenzodiazepine



• N-arylation


• dehydration


• propionaldehyde 원료


• malonitrile

quetiapine

risperidone

4-[2-[4-(6-fluorobenzoisoxazol-3-yl)-1-piperidyl]ethyl]-3-methyl-2,6-diazabicyclodeca-1,3-dien-5-one



fluorobutyrophenone


4번 탄소에 3급 아민기 치환 필수


• propyl 사슬 변화시 활성 감소


carbonyl기 최적



• Friedel-Crafts acylation


• N-acylation


• Oxime formation


• O-arylation


1,3-Difluorobenzene 원료


1-Acetylpiperidine-4-carbonyl chloride 원료


2-Aminopyridine 원료


3-Acetylbutyrolactone 원료

domperidone

carbamazepine

5H-dibenzoazepine-5-carboxamide



Wohl Ziegler reaction (radical reaction)


2-nitrotoluene 원료


• phosgen 원료

valproic acid

2-propylpentanoic acid



• Retro-Claisen reaction


diethyl malonate 원료


n-propyl bromide 원료


• ethyl acetoacetate 원료

lamotrigine

6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine



• Grignard reaction


• 2,3-dicholoro-1-iodobenzene 원료


• 2,3-dichlorobenzoic acid 원료


• dichlorosulfoxide 원료


• Cuprous cyanide 원료


• 2,3-dichlorobenzyl cyanide 원료


• aminoguanidine 원료

naloxone

pentazocine

fentanyl

loperamide

levodopa

carbidopa

biperiden

atropine

ipratropium

oxybutynin

donepezil

epinephrine

phenylephrine

salbutamol

formoterol

fenoterol

alfuzosin

propranolol

atenolol

carvedilol

amitriptyline

fluoxetine

paroxetine

ondansetron

sumatriptan

lidocaine

dibucaine

sildenafil

vardenafil

theophylline

ambroxol

montelukast

pranlukast

amiodarone

doxapram

verapamil

diltiazem

nifedipine

amlodipine

enalapril

ramipril

benazepril

valsartan

hydrochlorothiazide

furosemide

simvastatin

atorvastatin

clopidogrel

cilostazol

glimepiride

acetaminophen

aspirin

dexibuprofen

diclofenac

piroxicam

bendazac

sulindac

indomethacin

hydroxyzine

cetirizine

fexofenadine

loratadine

methylphenidate

acyclovir

modafinil

esomeprazole

pyrazinamide

chloramphenicol

orlistat

levofloxacin

methotrexate

ketoconazole

ciprofloxacin

propylthiouracil

fluconazole

imatinib

cyclophosphamide

amoxicillin

levothyroxine

mefloquine

cimetidine

isoniazid

cefaclor

ranitidine

tamoxifen

oseltamivir

5-fluorouracil

doxorubicin

metronidazole