Heterocycles Reversed Flashcards
1
Q
saturated 8-membered heterocycles
unsaturated
A
-ocane
-ocine
2
Q
A
azepine
-ine 7 membered UNSATURATED
3
Q
A
benzoxazole
4
Q
A
benzothiazole
5
Q
A
cabapenems
6
Q
A
pKa’s of
Pyridine
Pyridazine
Pyrimidine
Pyrazine
7
Q
A
carbacephems
8
Q
A
Aziridine
-idine for Nitrogens (3 membered staturated)
9
Q
A
penam
10
Q
A
tetrazole
11
Q
A
morpholine
12
Q
A
1,2-diazepane
13
Q
A
cinnoline
14
Q
A
cepham
15
Q
A
Thiirane
-irane for 3 membered rings (saturated)
16
Q
A
penams
17
Q
A
adenine
18
Q
A
isoxazole
1,2-oxazole
19
Q
A
1,4-diazepane
20
Q
A
quinoline
21
Q
A
oxapenams
22
Q
A
Order of Reactivity
Beta Lactams
23
Q
A
furan
24
Q
A
benzotriazole
25
Alcohol = 1
Amide = 1
imidazole = 1
pyrrole = 1
1\*(primary) amine = 2
H-Bond Donors
26
pyrid**ine**
-ine 6 membered unsaturated
27
saturated 6-membered heterocycle
_unsaturated (aromatic)_
-inane
_-ine_
28
ceph**_ems_**
29
pen**_ems_**
30
saturated 5-membered heterocycles
_unsaturated_
saturated w/ NITROGEN
-olane
_-ole_
-olidine
31
purine
32
pyrrole
33
tetrahydrothioph**_ene_**
34
thioph**_ene_**
35
1h-benzo[b][1,4]diazep**_ine_**
36
oxaceph**_ems_**
37
**iso**thiazole
**1,2**-thiazole
38
1,2,3-triazole
39
quina**zo**line
40
Xanthines
41
monobactams
42
indole
43
piperidine
44
pyrrolidine
45
azep**_ane_**
## Footnote
*-ane 7 membered saturated*
46
tetrohydrofuran
47
1,4-thiazep**_ine_**
48
saturated 10-membered heterocycle
_unsaturated_
- ecane
- ecine
49
thiepane
50
1,3-**dithietane**
51
saturated 9-membered heterocycle
_unsaturated_
-onane
_-onine_
52
Thietane
53
1,3-diazepane
54
benzo[b][1,4]thiazep**_ine_**
55
imidazole
56
pyridazine
57
S\>O\>N
Order of Increasing logP = Lipophilicity (SOLUBILITY)
N\>O\>S
Order of Increasing POLARITY
logP trends
58
**iso**quinoline
59
1H-1,4-diazep**_ine_**
60
thiep**_ine_**
61
saturated 4-membered herterocycle
_unsaturated_
saturated w/ NITROGEN
-etane
_-ete_
-etidine
62
**benzo**thioph**_ene_**
63
carbapenams
64
saturated 7-membered heterocycles
_unsaturated_
-epane
_-epine_
65
Ox**irane**
66
thiazole
1,3-thiazole
67
pyrimidine
pyrimidine
68
Ketone = 2
Ether = 2
Imine = 1
Oxazole = 1
H-Bond Acceptors
69
Az**etidine**
## Footnote
*-etidine for N 4 membered sat rings*
70
Ox**etane**
**-etane** 4 membered saturated ring
71
quino**xa**line
72
guanine
73
ceph**_em_**
74
pyrazine
75
clavams
76
L-proline
77
**benzo**imidazole
78
beta-lactam
79
saturated 3-membered Heterocycle
_unsaturated (double bonds)_
saturated w/ NITROGEN (aza-)
-irane
_-irane_
-iridine
80
1,2,4-triazole
81
90%\> likely that compounds with 2+ of these characteristics will have poor absorption properties
lipinski's rule of 5
**Poor oral absorption** and/or **distribution** are _more likely_ when:
82
pen**_em_**
83
oxazole
1,3-oxazole
