Contents
• Introduction of Steroids
• Nomenclature
• Sex Honnones
• Biosynthesis of sex honnoncs
• Structure, synthesis of Testosterone, Ocstriol, Ocstradiol, Diethyl
stilbcstrol, Progesterone
• Reference
2
-
Introduction
• Steroids arc a unique class of chen1ical compounds found widely in
the animal and plant kingdom.
• These arc characterized by the presence of 1,2-
cyclopcntanoperhydrophenanthrene nucleus in their structure.
• The steroids include a wide variety of naturally occurring synthetic
substances such as stcrols. bile acids. sex honnoncs. adrenal
cortical, various contraceptive drugs, cardiac-active lactoncs
sapogenins and certain alkaloids and antibiotics.
u C!iJ •
I
I If
C II
I ~ f
' .\
10 8 8
J
'
Steroid backbone
3
• The 1enn cholesterol was derived from the Greek words bile (which
means chole) and so1id ([Link] meaPS sterols). The :m odem era of
steroid research began with stcro,ids chemis lry in. l 900's~ [Link]
1
WindaL1s worked for 20 years and received the noble prrize in ]928
for his research on 1he cons t itlltion of sierols..
1
• Dr. He'inricb and W·ietand engaged in narura.l products chemi:stry
h1cludi11g bile acids and were awarded the nob le priz.e in 1928 ~
• A total of 6 noble prizes 'Were awarded to [Link] woiking in lhe
area of steroids,. among dt.e 6!4 prizes] were ·m steroid chemistry
,category. The pioneer, work of the Adolf Wind·u as and Heinrich
1
Wh:land in the structure elucidation of' ,a number i·m porlant steroid
led ·t o the .[Link] d [Link]-overies ·in the world. of steroids.
• The two importanl discoveries mentioned in. 1940 and 1950 had a
dramatic effect not only on lhe sleroids. This led to an e,xtensi·ve
research om medicinal cbemistry1, [Link] and clinical s1udies
,o f stero,ids against and antagonists.
• The steroids are Found as solids a1t1d M.P .nmges m,,m IO()OC to
.2500C~ insoluble in water, soluble in ethanol, acetone·" chlorofbrm1
1
(Organic Solvents).
Nomenclature
I. Steroids consist of 4 fused rings (A, B, C and D). Chemically these
hydrocarbons. Arc cyclopcntanopcrhydrophcnanthrcnes. They
contain S mcn1bcred cyclopcntanc (ring-D) and the 3 rings of
phenanthrene (A, B, C).
II
l
.• .\ 8 I
2. Earlier the various steroids are generally designated by their
co1nmon names such as cholesterol, progesterone, and testosterone.
However these names were discarded due to development in
che1nistry and systemic nan1es as per IUPAC no1nenclature were
favoured.
r,
J ~ Staroids contain 17 carbon atoms and the numberin:g the remaining
carbons of phenanthrene [Link] by numbering lhe remaining
carbons of tile. cyclopenlane ring. .Additional carbon atoms. on the
:sler,0 ids including metlllyl groups attached to C-10 and Cw 13 ,ond
1
alkyl 'Substirue-nt ',[Link] c. ..17 ar-e numbered~
4-. [f any uasaluretiom is present in. the steroids the ane endjn_g of' the
1
stem is replacing: by ene if it contains one double bound, dlene if it
contains. lwo daub:le bounds, trlen, ilf it contains three double
1
'bounds.
S. lf double bound is not between carbons both the carbons are
indicated as u me,.
6. If the steroid contain J-n1embered rins il is indicated by the prefix
cyclo preceded by the numbers ofposUions concerned.
1
7. Any enlargement of steroid ring is indicated by the prefix homo
1
preeeded by small capital indicating the rins affected.
8. Circtes were sometime.s used ro indica·te cr-bydrogens and dark dots
are used 10 indicate P,.hydrogens~
9"0n the basis of followin,g priorities suffi:x fo.r stem name is se,lected
carbo,[Link] acid> carbonyl> alcoho l> amine> etherm
• Hormones are 'the organic substances whicb are secreted by
the
endoeri ne g)ands.
• The y are brought to ·the different organs of the bod y
by means of
blood stream to pro duc e the various .Physiological functions~
cur ed
• The detlciency of honnone leads to particular d'isease can be
by [Link] of bon non e.
-
Classification
• Steroid honnoncs arc divided into two types Sex honnoncs (male
and female) and adrenal cortical horn1ones
S1e...W..
I
I
SN •••roiib
Sirs lloraoatt~
l
I
1 l
1
Ontrosn
l
• Sex honnoncs are produced in gonads (testes in male and ovaries in
fe1nalc). Their production is stimulated by pituitary gland.
10
Biosynthesis of sex hormones
o.w,...i
Siok •b• I
~
~
t ..-a ~>"°~~-b_~/
0
/ -.j,..-<. O< 0
-
•
H H
17•- ~,4,...,.
.,..■Nole••
l,...lOl)-aH 1
11
0
. -,
-
- H
1lloJil .p,,"5rln11 Alnsttl&1e lslnll
i?•hffH!'dr01J'5 lermd
11fiiydropme
jf [slnrlial
jl ~1JOJH1U
I
OH
~ wJ11cbJ!
4 --
TlilSINe
EslrJ•I
1 • 'JT
.'
estosterone:
. , - 1 2 6 1.s .9 . n
JUP'.AC: 11-\-l . .
ydr-oxy- 1o 1 3 - d u n e lh Y ~ ' . 1 2.1 4. l S . 1 6 ,
dodecabydrocy "i [ a l p h e n a n lh r e ' \ i·
e\ope1l' n-3-one
OH
10
J t.
Molecu\aT Farm
In \935 Testoster ula: c,.11 O-z
one was isolated 21
b y E . 'Laque r u
e t a \ .. f r o m t e
stes .
Synthesis:
-
.~
II,
i!r. . .
HH
:,.
ClltoOII 9 I,
0 • r;: O •
~: O • '
Cl
'
a.
1W1111Wii- -
iiNllliit
AC:()
l:>[Link]
9
!!O '
c: O
I
C&«J(l
'
Cl llill~
1·•
OC.c.H,
HO
Oppt.w1Hr
l Odd1tl..
fe1tostBm1e EaudaaN
15
Properties and Uses:
• Creamy white crystalline powder, insoluble in water and soluble in
alcohol.
• It may be used for treatment of breast carcinoma in postmenopausal
women.
16
2. Qestriol: . 4 15 1 6 1 7-d ec ab y d ro cy cl o p en ta
lU P A C : 1J ...methy l....6~!
,B,li9 :l l . l2,.1 • ~ ,. [a l
pllenanlbrene-3.1 6, I7- lflo
I
14-
3
H
-
O/
4
Cl
M
olecula r ·t :o n n u la : C
It is isolated b y Marti
an from u ri n e o f preg 1aH24OJ
in somecases o f oestrogen de6 nant w o m en
. It is u se fu l
menopausal sy1nptoms. eo cy es p ec ially for th e re li e f o
women.
It o cc u rs m ainly in placenta a n d f
p re g n a n t
Synthesis:
• Route-I
11,C 0 oAC
11,C
uoproptm ...1...
H
. .
H H H
HO
-- ACO
CdbCOOD
Ptrbc.111cic acid
QAC
H~ °"I Olt H,C - ;-9
/' l. LWJ!, H
.
H
ACO
Onlriol
18
• Route-2:
CH,
H CH, 0
oCSHuO~a CH,S(J!
!1-ent
H oa
H 0
(CJIJ)iCOK CB.,CO,.H
--
Mia,lt111rif it it
I
H,CO
11,<X)
:il(Cl!J):(808
Cl
JI Cl CH, (II
lllk H OB
(Y ,.- ClilCO-.H it
.,(VV
llllrill
Q e s . ·d~ 1~
tr
3• --
a ·~10 • - , deca-1 ~l, S -t n•·ene:- 3 ' t 7 -d iOi I
• 11
lh
1IJP:AC·:. 1J-rne y•ltctracYclo he pt a
1: H, C ~ 1-
LI I lli
I J" I!
8
Molec u lu F•o·rmula: C
1
11H u 0 2
I~ ex·ists ~s two stere_oisom
1csomers 1s more· actave o ~ric o ~ tr ad io ls (4:1 an d P) b et w ee n th
111... 1somer 1s le ss ac t1 ve .. 1
e m l3-
Synthesis:
Li.\114
H H, , -
/--
I '-:: H H Aluminium isopropoxide
1'-:: HH
HO A HO A
oeslrOH
Oestndiol
21
4. Diethyl stilbestroJ:
iethyl- l ,2-etbencffiyl]blspher
II/PAC: 4,4'•[ J)-D
3
Z
c,
B c': .
'C:Bs
Molttular Fann11hl: C111fmO,
Synthesis:
1: fn ,m antsaJdehyde (Dodd5 Met flod)
• Melhod-
11.'.C~ "' 11,CO <~ -, ·. - CO~
,......,
---~
IN D ... .,_ or
....
.,
jso.1 i:
•COOOCII,
- ' f: B IC .' 7 ca.
• a..::::~ l • i \.j""o
Ir th. ua fir KO U
•
~ C: &, · -
-. ., ~ l, . . ~ l OB
•1 1 :t 1 ~
• [Link]-2: From Anethole
B
2 n,co ,
• c-CJIJ no,__
_
AucWe
_F\ C:&, C:"r-\
FIJCO"'t.!/Clfa i V OCBJ
1Alluli
B
-O c:e."
~:
c,ru
~ /
~ylslil>Htrol
OB
..., ..
S. Progesterone:
• Progesterone means favoring pregnancy. These are substances in the
Corpus Luteum. Which convert the oestrogen-primed endometrium
to secre1ory endometrium and maintain pregnancy
• Progesterone was isolated from the Corpus Luteu1n, the adrenal
[Link], the placenta and testes.
IUPAC: 17-acetyl-10, 13-dimethyl-l ,2,6,7,8,9, 11 , 12, 14, 15, 16, 17-
dodecahydrocyclopenta[a]phcnanthren-3-onc
CH,
I
c=o
"H, In
II II
IJ
l 15
I
J
0 ,,:::-
Molttular Formula:C 11 H300 2
25
Synthesis:
•
··-~
/"...u"..-.... ..,,
0
• CtOJ,CllJCOUtl
.
'• ~c...-0044 H
H
•• o.1 .• , · 1 -
l
.lC :0
QI, ~
IIO;i. Cl
"' H POClt • ,,, --
.
H
• L'f'C
ACO
QI,
ot,
'
co co
• H
'•
H
0
Pt .
26