Arsenicals containing a pyridine nucleus

41 Pages·05.022 MB·English

by  Hatlelid, Elbert L.

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X* Introduction . . . . . . . . . . . . . * . . . . . ' 1
XX* irej&jitaX lepreeentation of Ite&otioae* * * , * * * $
XXX* Discussion . . . . . . . . . . . . . . . . . . . . 7
If* BxperXffient&l * * * * * » . • • • » # » • « . . • * X®
A# Preparation of 2-{p«araonophenylaraino)-3-
nitr ©pyridine and related eoi8p©und8, * * * * * X®
1* 2 -Ohlor© ~$ «*ni tropyrldlne
2* 2-Cp~Aalnophenylaaino)-5-.nitropyrldin©
3. 2 - Cp-Arsonophenylintln©) *5 -nitr ©pyridine
4 * 2-(p -Ar ® enosophenylasiino} -5 -at tr ©pyridine
S# 2-(p-Arsonopbienylaiaino)-S«a!ninopyridine
6* 4-£2* -(5* -AidinopyridylJJ-aialnophenyl-
ar seal ©tie acid
1* freparatlon of 2 - (a-araonophenylaiaiBQ) -5 -
■ nitr ©pyridine and related oompsnmde* * * ♦ * .* li
7, 2-(««Jy®ln©phenyla®ln©) -S -nitropyridtne
8. 2*<m»Arsofnophenylamin©)-6-*nltropyrldine
9 • 2- (ei-Ar senosopiienyla®ino) ~S *ni tr ©pyridine
10* 2 - (m-Ar eonophenylamino} -5 -aainopyrt&ine
#* Preparation of 2- (1* -benssotriaeolyl} -S-arsono-
pyridine and related compomda # * * , , * * *. 21
11* 2- (o-Aiainopheaylsod.no) -5 -nitr ©pyridine
12. 2-(l*-Beneotriaeolyl)-5-nitropyridine
12* 2-(l* -Benaotriaaolyl)*5-aninopyrldlne
14* 2-cl*-Benaotriezolyl)-5-areonopyridlne
IS. 2-fl1 -Benaotriaaolyl) -S-areenoaopyridine
U* Preparation of 3-ni tro-4 - (p -arsonophenyl-
anino)-pyridine and related compounds, * * * * 2§
16 * Chelidonlc acid
17, Ohelidaxalc acid
18, The nitrate salt of 4-hydraxypyrldlne
19* 3 -Ifi tr © -4 -hydroxypyridlne
20, The hydrochloride of 3<-nitro*4<*©hl©r©-
pyrldine
21 * 3 -N1 tr o-4 - (p -aminophenylamiao) -pyridine
22# 3-Hltro-4-ip-ar®«no|rib.ei»l»diio)-pyridine.
23, 4 - £4* - (3* -litropyridyl) J -amtnophenyl -
arsaniouo aold
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1* "tatrodnotion
1
Since Shrlleh* e ayntkssi s of a^aphenajolii© the useful*
ness of organic derivatives -of arseni© in'the "field-of
chemotherapy has steadily-increased* However, Ike met'-of
Many of such mwm&mX® is United because of Ike t«ati©iby*
caused by their astiOn# toward the human system.
2a this connection the me# Of two organ!© arsenleala ■
will be briefly reviewed* • ■
Atm yl {Ike »«ao*e@ilw eell ©f p*e®la^toeiylttr»«ftie
aeidj Is M©r® ©ff©otiv© th*** inorganic ' srsonlo In the
tr®ati&tet of teypte©s©*®laai## However, Iks drug 1» espe*
eially dangerous beoam®.® of ©file injury and blindness
which result Mai il* use, ■ ■■
fiypsy§*SBid# (4 -arsonophenylglyoineamide), derived
■ t ■
trm at©*yl by Jacobs end B®id®ib©a?i©pf le need in the
tr®at»««ib of' Idle central nervous. systte ■ syphilis m S in
trypttoscwlasls* Cases of ©ft!©' injury and blindness have
resulted also from the mm of Ibis tohpONMft*
lino# no I*pyfiay!*4teiwaily*« of p~a»in©ph©nyi~
arsonle aeld have been reported in the literature ted be*
d#-d
cause Bins ted Balk ' have found that certain d-substi- '
luted derivatives of b«te*te©ffridi»® have therapeutic value
It was the purpose of this investigatlte to study organ!©
arsenical® of the following b|jt«#t
1. H-Pyrldyl- derivatives Of p-amlnophenyl&rson!e sold
which also otetained a free ante©- gromp on the pyridine
nuoleus*
.§
Sinse the'.start of the investigation, infoi»ti«
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t* ,
has been re©®fve4 to the effeeb that a m©lamia© dertw*
ative of p •as&nophenylar sonie aeid width- probably ha®
the following atnwetm1©
H HHa
a . . H /H=CV
t O ' - w
H MR*
has been used affectively In the treatment of aleeping.
sickness and 1a -reported to have little or no .,■■■.
offset upon the ©ptie nerve*
$* I~Pyridyl~ derivatives of m#easiao^enflar#oai«
aeid abieh'alae have a free ipia® gritf on the pyridine. -
aaelema*
dliiioiigii it ie diffienlb to establish any tafalil*
bl© rale*.'relating eihwalftaX e«etitatl* *»d therapeutic
&et3 vity, ¥©mg and hoeventoart: observed that
tonicity fw the opt!# nerve appear* to be connected
with - the siiiatt tubed ante© group in. the pOeitfoa para*
to the arsenic. Similar aoapoaariUi with the araenio in
the ortho* or note* poeltioii are apparently free of
thle danger*
3 . a *(i» • ^ a a o tria a ® ly l)* i« a r* « o ^ rid in e *
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