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Medicinal chemistry > alkaloids 1 > Flashcards

alkaloids 1 Flashcards

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1
Q

confers the basicity of alkaloids, facilitating isolation and purification

A

nitrogen atoms

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2
Q

low molecular weight nitrogen containing compounds

A

alkaloids

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3
Q

alkaloids came from the word

A

alkali

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4
Q

the degree of basicity of alkaloids varies greatly depending on

A

structure of alkaloid molecule

presence and location of other functional groups

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5
Q

true or false.
the biological activity of many alkaloids is dependent on the amine function being transformed into quarternary system by protonation at physiological pH values.

A

true

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6
Q

the subdivisions of alkaloids into groups are based on

A

amino acid precursors

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7
Q

true or false
the carbon skeleton of particular aa precursor is retained intact in alkaloid structure but carboxylic acid carbon is often lost through decarboxylation

A

true

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8
Q

true or false
a large group of alkaloids are found to acquire their nitogen atoms via transamination reactions, incorporating nitrogen from amino acid, while the rest of the molecule may be derived from acetate and shikimate

A

true

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9
Q

alkaloids that are terpenoid or steroid in origin are called

A

pseudoalkaloid

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10
Q

what are the alkaloids derived from ornithine

A

polyamines
pyrrolidine and tropane alkaloids
pyrrolizidine alkaloids

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11
Q

non protein amino acid that comes from the urea cycle in animals

A

L-ornithine

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12
Q

supplies the C4N building blocks

A

ornithine

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13
Q

in animals, l- ornithine is produced from ( ) catalysed by arginase

A

arginine

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14
Q

in plants, l- ornithine is formed from

A

l- glutamic acid

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15
Q

ornithine supplies C4N building block principally as

A

pyrrolidine ring

tropane ring

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16
Q

Critical regulators of cell growth, differentiation, aand cell death

A

polyamines

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17
Q

examples of polyamines

A

putrescine
spermine
spermidine

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18
Q

it is the important target for chemotherapy

A

poylamine pathway

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19
Q

up regulates P53, tumor suppressor protein

A

polyamine analogues

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20
Q

combats cancer by inhibiting proliferation of cancer cells and increase apoptosis

A

polyamine analogues

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21
Q

reduced aging of yeast cells

A

spermidine

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22
Q

characteristic odors of sperm

A

spermine

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23
Q

drug target in malaria parasite

A

spermidine synthase

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24
Q

sci name of malaria parasite

A

Plasmodium falciparum

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25
Q

example of pyrrolidine

A

hygrine

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26
Q

isolated by Carl Liebermann as an alkaloid accompanying cocaine in cola

A

hygrine

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27
Q

it is exracted as thick yellow oil wit h a pungent taste and odor

A

hygrine

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28
Q

hygrine and N methyl delta 1 pyrrolinium cation inetrmolecular mannich reaction results to

A

cuscohygrine

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29
Q

Tropane alkaloids occur in many members of plant family

A

Solanaceae

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30
Q

main classes of tropane alkaloids

A

anticholinergics ( atropine, hyocyamine, scopolamine)

stimulants ( cocaine, ecgonine, benzoylecgonine, hydroxytropacocaine, methylecgonine cinnamate)

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31
Q

alkaloid that is synthetic precursor of atropine

A

tropinone

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32
Q

Tropinone gives rise to

A

calystegines

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33
Q

a water soluble and polyhydroxy nortropane derivatives

A

calystegines

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34
Q

isolated from Calystegia sepium ( convolvulaceae)

A

calystegines

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35
Q

Glycosidase inhibitors

A

calystegin A3 and B2

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36
Q

have the potential for the development of drugs with activity against AIDS virus, or HIV

A

calystegines

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37
Q

Formed from tropinone via tropine

A

hyoscyamine

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38
Q

ester of tropine with S tropic acid,whichis formed from l phenylalanine and phenyl lactic acid

A

hyoscyamine

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39
Q

intermediate whoch undergoes rearrangement reaction to form hyoscyamine

A

littorine

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40
Q

-(- hyoscine) aka

A

scopolamine

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41
Q

hyoscyamine and hyoscine are important alkaloids found in

A 
atropa belladonna ( deadly nightshade)
datura stramonium ( thornapple)
hyoscyamus niger (henbane)
Duboisia spevies
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42
Q

responsible for toxic properties of nightshade, thornapple, and henbane

A

hyoscyamine

hyoscine

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43
Q

Cocaine biological source

A

Erythroxylum coca (erythroxylaceae)

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44
Q

diester of ecgonine

A

cocaine

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45
Q

used as local anesthetic and illicit drug for its euphoric properties

A

cocaine

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46
Q

ecgonine comes from benzoyl coa derived from blank via blank

A

phenylalanine

cinnamic acid

47
Q

anatoxin a is from 2 cyanobacteria

A

Anabaena flos-aquae

Aphanizomenon flos aquae

48
Q

termed as very fast death factor

A

anatoxin a

49
Q

powerful agonist of nicotinic acetylcholine receptor

A

anatoxin a

50
Q

useful pharmacological probe for elucidating the mechanism of acetylcholine mediated neurotransmission and disease states associated with this process

A

anatoxin a

51
Q

anatoxin a has what ring system

A

homotropane

52
Q

T/F the reamining carbons of anatoxin a is from acetate pathway

A

true

53
Q

from highly colored skin of Ecuadorian frog

A

Epibatidine

54
Q

sci name of Ecuadorian frog

A

Epipedobates tricolor

55
Q

epibatidine has what ring system

A

nortropane

56
Q

lead compound for analgesic compounds

A

epibatidine

57
Q

200-500 more potent than morphine

A

epibatidine

58
Q

act as agonist of the nicotinic acetylcholine receptor not the usual opiod mechanism

A

epibatidine

59
Q

pyrrolizidine is widely distributed in

A

Boraginaceae ( Heliotropium, Cynoglossum and Symphytum)
Compositae/Asteraceae (Senecio)
Leguminosae/Fabaceae (Crotalaria)

60
Q

occurs ias free form but most in ester with mono or dibasic acids- necic acids

A

pyrrolizidine

61
Q

hepatotoxic agent prolonged use as herbal remedy for inflammation, rheumatism, GIT disorder, and toxicity

A

acetyl intermedine/ acetyl lycopsamine

62
Q

potent antileukemic agent

A

indicine n oxide

63
Q

indicine n oxide comes from

A

Heliotropium indicum (Boraginaceae)

64
Q

alkaloids derived from lysine

A

piperidine
quinolizidine
indolizidine

65
Q

precursor for alkaloids providing 6 piperidine ring and 5 pyrrolidine ring

A

l lysine

66
Q

N methyl pelletierine is present in

A

Punica granatum (Punicaceae)

67
Q

having activity against intestinal tapeworms

A

pseudopelletierine
N methy pelletierine
pelletierine

68
Q

homologue of hygriene

A

n methylpelletierine

69
Q

homologue of tropinone

A

pseudopelletierine

70
Q

analogue of cuscohygriene

A

anaferine

71
Q

anaferine comes from

A

Withania somnifera Solanaceae

72
Q

true or false benzoylacetyl coa comes from shikimate pathway by cinnamic acid

A

true

73
Q

true or false 2 intermolecular mannich rxn and reduction to form lobeline and lobelanine

A

true

74
Q

lobeline comes from

A

Lobelia inflata

75
Q

use as for smoking cessation and anti- asthmatic

A

lobeline

76
Q

sedamine comes from

A

Sedum acre (Crassulaceae)

77
Q

Piperine has piperoyl coa that comes from shikimate and acetyl pathway

A

true

78
Q

from black pepper

A

piperine

79
Q

black pepper sci name

A

Piper nigrum (piperaceae)

80
Q

used as condiment

A

piperine

81
Q

forms tertiary amide as it condenses with piperic acid CoAsh ester

A

piperine

82
Q

homologs of pyrrolizidine

A

quinolizidine

83
Q

quinolizidine is found in

A

Leguminosae

Laburnum, Cytisus, Lupinus plants

84
Q

repel feeding herbivores and responsible for human poisoning

A

quinolizidine

85
Q

from lysine via cadaverine intermediate

A

quinolizidine

86
Q

Lupinine is from

A

Lupinus luteus ( Fabaceae)

87
Q

Sparteine is from

A

Cystisus scoparius fabaceae

88
Q

indolizidine alkaloids are found in

A

fabaceae ( swainsona, astragalus, oxytropis)

89
Q

hybrid of pyrrolizidine and quinolizidine alkaloids

A

indolizidine alkaloids

90
Q

from lysine via L pipecolic acid

A

indolizidine alkaloids

91
Q

toxic compound from Laburnum sp fabaceae

A

cytisine

92
Q

castanospermine and swainsonine comes from

A

Castanospernum australe- moreton bay chestnut
Swainsona canescens
fabaceae

93
Q

polyhydroxyindolizidines

A

castanospermine

swainsonine

94
Q

inhibits glycosidase in glycoprotein biosynthesis

A

castanospermine and swainsonine

95
Q

activity against AIDS

A

castanospermine and swainsonine

96
Q

causes severe GIT upset and malnutrition by inhibiting hydrolase enzymes

A

castanospermine and swainsonine

97
Q

alkaloids defived from nicotinic acid

A

pyridine alkaloids

98
Q

aka nicotinic acid

A

niacin

99
Q

important component od coenzyme NAD and NADP

A

pyridine units

100
Q

in animals nicotinic acid arise from

A

l tryptophan

101
Q

in plants nicotinic acid arise from

A

3 phosphoglyceraldehyde

L aspartate - not sure

102
Q

nicotine comes from

A

nicotiana tabacum solanaceae

103
Q

nicotine structure consists of

A

pyridine ring - nicotinic acid

pyrrolidine ring - L ornithine

104
Q

nicotine is oily and volatile liquid alkaloid

A

true

105
Q

comes from nicotinic acid with piperidine and pyridine ring

A

anabasine

106
Q

derived from 2 moles nicotinic acid

A

anatabine

107
Q

delta 3 piperideine ring of anatabine does not come from l lysine

A

true

108
Q

toxic compound from castor oil ( ricinus communis euphorbiaceae)

A

ricinine

109
Q

formed from dehydration of nicotinamide derivative

A

ricinine

110
Q

tetrahydronicoyinic acid

A

arecoline

111
Q

from betel nuts

A

arecoline

112
Q

betel nuts sci name

A

areca catechu arecaceae

113
Q

has stimulant effect and agonist of muscarinic receptor

A

arecoline

114
Q

used as vermicide in veterinary practice

A

arecoline

Medicinal chemistry (6 decks)

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