.

Iming R. 8her and Eugene Garfield Institute foac Sczientific Information

I A k v i c e ir nuu available through which an individual

may oubrait a vide variety OF queatioaro in the form of M ASCA

profAlo and 2m alerted on &ran+ snd perscmal bad8 to tho /

mart recent Ziteratuza sulated to hie intersatr (Figure 1). The

,

w i t h the AGCA BymtAw8 oimply in to the c i tat ion identifying the

article by Arroyo, namely, aArroyo 6.R. . Chm. & Xnd,, pp. 350-

351, 196S.(2) In the bibliography of the Arroyo pager, the uber

would 81.0 have been made maro of additional earlier work8 that

rtudied tho structure of t h i s compound (Figure 3)* Any of theme

alw may be entered 88 queetiona i n the 2UCA profile.

to the Hecker articlr would, for example, s e e m particularly

Reference 3

appropriate a8 mhaua in the commentary by-Arroyo about thio r e f e r

eace, naraaly, "'Hora recently an amorphauo sctive fraction from

croton oil was hsolated, and some structural conclusions were

in the ir attempt8 to obtain JB czyrrblline Campcrund." The chemht

would then receive in hi8 weekly ASCA conrguter: printout. 8 corn-

pleta description of a l l the current uotko which cite any of

theme referanrcer indicated i n the profile. For example8 m o o n

after its original publication, t h i n chedrt would have basn

inforasd by ASCA that the Arroyo paper wa8 cited by Z i e d k r r ' m

eri (Figure 4)* (4) . group i n an article appaxing in Tetrahedrog ktt

If he had entered reference 3 fzaa the Arroyo paper a8 a quemtion

it w o u l d h8ve .erved the same purgooe. \

X f he had exatmrod both

the A r r o y o and the third reference a8 qUeOtiama, tho AX% print-

out -14 have indicated that both were crited by the~amu Eecket

.

i

- 3 -

among other thing@# new additional infomation on the phyafcal

propertiem of the n w conptnmd,

OMer varistles of ABCA gueiltiono could have also retrieved

this nuu papex8 but y8 shall confine ouroelvm here to dimuomiom

of citation questions only,

As our seccnrd exrurrgle, let's II~PUWB the c h & d s t is inter-

ested in mynthetic method# for des~cetylamin~colc~kiceine. Thia

compound is of biological interest and ir be- employed 3ip

chemist., pharmacologimto, and ghysiciano in experimental biology

and therapeutic to~earch.

of thim caogaund mruld have baen expraowtd, for hie A m profile,

in term0 of citations identifying the earlier known work. 01s

The chemistor interest in the a p t h e d o

the subject. m i g h t have entered qusstio~s, for instance,

for *Van Tamelan tT;.%# Fetrahcdroq 148 8 (1961)1(') and f ~ l t

*mrtel so, C.R. *ad mi8 250, 243 ( 1 9 6 ~ ) 9 6 )

question. would have resulted An notification of the C u r r e R t

appearance of paper by #artel 3. 0t a1 in 30i6) , 1752, June 1965 entitled "A Hew Syrrthemi8 of btssacetaaridocalchi-

,

Sither of theso

\

the namnclrture prdblemm and even the variant spellings of

the name of a apercific c a a g ~ ~ n d i n different languages. The

colchidm* w h i l e in the 1965 gaper (in gA Om, C&&.) it As

Bgrlled a~eaace~~i~ocolchicein~oa Citation im?ex’i&ng associates

these t w o p a w s in spite of t h i s differenoe and, in fact, wauld ,

have done mo even if the conppaund were net named in the title

or even in the article it~slf. i

?nv39retiuat&m e$? B. loloctical Activ- of IR Connoun d

In tho third example, let us illuertrate how the cheraiolt

interested in foll.ariag the biological development of a caqpound

would bo ~rtbrved by ASCA.

Chen‘” might be the rtrrting p i n t .

Kniawl&g+ of tbe w o r k by XcCarthy end

fn thio paper the anerrthetic

action of CI-381 war0 demonstrated h monkey#. The McCarthy article,

entered aa a question Am ASCA, would resu l t in m alert describing

the mom recent paper by Dorcrino, Chodaff, and Corsoan in which

the drug was tested in 20 prieon volunteers, In thirr first human

B x t e ~ f e r m of wark util izing a type of reaction can bs . .

Tbe citation indexing principle in ASCA, hawever, quite readily

leads frau the papgra reporting a type of reaction to the papera

which apply or extend thie repaceion. Thio AzicA sdect iv i ty fun-

t i o ~ unimpaired even though the reaction may have no fdentffying

nama or epym and evsn though the o t s r t h g mtarialia and/or end

productm may vary greatly. ,

The paper by Parham (lo) describes the preparation of tetra-

hydropyranyl derivatives of alcohols and pharaoh. ASCA would

alert tbs chemist interemted in abxtenaione of this work tothe

WPSr by GatQgg (lS). rsummiPrirhg several of him awn atudiea, in-

eluding the rqmrtwhelcein Caxegg rucceedd in reparating tha

optical irroarsra resulting from the addition of! a hydmxyl canpaund

to dihydropyran in acid media. Another unique advantage of

citation indexing can be illustrated w i t h t h b caue. !l!ha user

auke a question phraaad ao *Paleham WOE,, ,J. Am, Chem. Soc., 70 ,

4187, (1948)* and im alerted to the errtblst by Garegg which

starts on page 28 and ends on page 50,

123 references i n the bibliography.

I

The Garegg article liato

These references are the

i d e x i n g tennrP UPS^ in citat ion indexing.

G a r e g g m r t i C l e ie indrwed b such tremendous depth by M C A (123

index terns), the c h d o t uazl quickly pinpoint tha -fie

relatioarship of thr -egg paper: to hio awn interen-.

Yet even though the \

Th+ user

I . b - 0 . . #

- 6 -

merely &nerves that the Parham article i u , in t h i n caoa, R e f . 113

and readily loeateo the a p i f i c point in the text (in the middle

of page 45) where Garegg cite. R e f , 113 upd describes the rolrtion-

.hip betwen that reference and tlle nwar work.

III our fifth example let ue assume the chemist know. of

the findamental work by Bxockman and Muxfeldt (I2) on tha Pyntheeie

of the rctinanycin chromophora. The Brockarsn ar t iah might be

entered am part 02 I profile used to alert chedot8 to any new

campound oynthesitd in this family,

w o u l d later include the paper by Hauger: (13' on the oyntheairr of

The hi%^ notifitzationo

dercribe8 a mew purely chemical (not ~~llribiaiogical) arynthe~iu.

C O W S n of E r r o r 4 in the Pub1 ished Lite$atuxs 1

In the sj3tt)l e.xrmlple we illustrate buw ASCII even provider

alert. for the cormaction0 that may appcssr to M stroneoum

Using Paper Chromatography, d. CbmmatQgLt XS, 379-3924 196U) . .

would have alerted the MCB U I P ~ to the comceetiopa published

c - - ModLf1cat;Lon 09 Analvtbsl PIcaCed ures

Modifications in analytical groccidulcea can ba follo#ed by

entexing ASCA queat ima to the exiating literature on the

procedures Iavolv(lbd. Thuu, kncwledga of m y of oeveral ~S8&1f08

for continuous f low thin-layer chrosaetoglraphy (lS20) would have

alerted the user to t b paper mCoatbuoua P l a t Thin-bayer

Chromatography* by T.M. -0, MJ. Lynch anB Be& h a h e r , &

Chr.ma toa -1q 595 (1965) (21) wherein twa additional variations

of thin-layer chraaatograghy are Uarrcribed and illumtratad.

Hew Hethd olocrv

'

X w chemical methoaology can be called to the uaiex?*s

attentha with ASCA as illustrrtetd by the folluufng. Xf the

chadet were to enter ASCA questians which identify any of f m t (22-25) h* of tha early mthds for testing far ruZf#xidea,

(26) would recsiva notification of the reoent paper by tr ltsuchomalava

the A ~ C A aptera a3ce available. Theeat fncludrp, in addition to

,

author qumtian by manta of which the u m r can be alerted to

a l l current i t e m s which cite any work by a given first author,

(2) 84u~ce author question by maria of which the usex uan be

alerted to a l l the uurrent journal and patent publications of

a given author no mattex where h i s name appara i n the author-

ship, (3) patent ra$signee question, by means of which the uoer

ie alerted ta a l l current W.S. Portent8 assigned to a given

organization, (4) patent claesibication question which w i l l

alert the user to t h appearance of patents aaaigrmd to any

given patent cleraifioatian number the 0,s. Patent O f f i c e ,

(3) organhationel queatiun which w i l l notify the uselt of a l l

the journaL publications attributed to a gfvcan corporation,

institution, QT sther organfaation, These sprscial indexing

approacham to the literature, coupled w i t h the blcoad (multi-

disciplhary) ma comprehensive (all jaurnrrls covered we

proceaoed in their entirety as .weall ae a l l U.8. Patents E~trued)

covorage of the weekly ASCA rep~brt~, can provide a eignifioant

8ervice for chemists and asoocfatsd ueera of thr literature

of scfmrocb an8t trrchnolqyy. \ ZI'UPI(I1EIARY

,

- 9 -

alerting oervice, Computer printout. are used to n e i f y

each client, at'weekly intervale, of the current article and

patents which aite any item in h i s intereat profile. The

referencoe ia tho bibliagraphieo of currsnt worka become the

indexing terms uued. The conceptual links established by these

bibliographic oitotfonrr provide the mano of eeleetiug appro-

priate iterne from a wide variety of pblfcotiona including per-

ipheral joutnals which might only publipah occasional items of

interest to a particular user. A t present more than 1,080

journalm 8nd a11 U.5. Patents iaousd are indexed on a very -

current basfe for ASCA. A variety of typae of queprtionsl m y

be entered in an A!%% profile, The ASCA a y B t e m allme the

w a r to add new questions 8t any time, as additional pertinent

worke are diecovered.

chemical literature can u t i l i z e ASCA will Be dclscxibed, including:

(1) alerting th8 user tcl additional works on a new compourrdt

Several ways in which the usetrtl 09 the

tion of bfolgical acrtivity of a compound; (I) new applfcationa

of a type of maation; (5) new ryrathssetta in a family of cornpcntndet

(6) coxmction of etrora in the published literature; (7) m o d i f i -

\

a t b n of analytical praceduxest a d ( 8 ) new rrtsthodology.

. -.. " ..

' , '-, .',t*:.: 1) Index Chemicus 17(3) , Abst rac t No. 50851 * . . L . .

* 2);,Eugene R. Arroyo and J. Holcomb, " I s o l a t i o n and S t r u c t u r e . Eluc ida t ion of a Highly Active P r i n c i p l e from Croton O i l , " Chem. & Indo tFebrua ry 20, 1965, pp. 350-351.

Al-First Pure Highlyh 8 o n s t i t u e n t of Croton O i l , " Angew. Chem. 3 ( 3 ) , 227 (1964)

. 4) E, Hecker, H. Kubinyi, Ch. von Szczepanski, E. Harle . . and H. Bresch, "Phorbol--- E i n Neues T e t r a c y c l i s c h e s

Diterpen aus Crotonol , " Tetrahedron Let ters , No. 23, ,

- , ' ' 3) E. Hecker, H. Bresch,I)c 7 . Ch. von Szczepanski, '*Cocarcinogen

.

. r

* . 1837-1842 , (1965). ' . 1

. .

E.E. Van Tamelen, T.A. Spencer, Jr., D.S. Al len , Jr., and R.L. Orv i s , Tetrahedron, 1 4 , 8 (1961). ?

J. Martel, E. Toromanoff, and C. Huynh, "Chimie Organique -- Synthese T o t a l e de l a Desacetylamino-colchiceine , " Compt, rend. , 258, 243 (1964).

J. Martel, E. Toromanoff, and C. Huynh, "A New Syn thes i s of Desacetamidocolchiceine," ,J. Org. Chem. 3 0 ( 6 ) , 1752 (1965)

--

D.A. McCarthy and G.M. Chen, "General A n e s t h e t i c Action of 2-(o-chlorophenyl) -2-methylamino cyclohexanone HC1 (CI-581) i n t h e Rhesus Monkey, Fed. Proc. 24, 268, (1965).

9) E.F. Domino, P. Chodoff, and G. Corssen, "Pharmacologic E f f e c t s of CI-581, a N e w D i s s o c i a t i v e A n e s t h e t i c , I n Man," C l in . Pharm. Therapeut . 6(3) , 279-291, (1965) .

10) W.E. Parham and E.L. Anderson, J. Am. Chem. Soc.,70, 4187, (1948). .

' ' 11) J. Garegg, "Studies on Some P a r t i a l l y S u b s t i t u t e d Glycosides and Polysacchar ides ," Svensk Kemisk T i d s k r i f t 77(1) , 28-50 (1965).

. 112) H. Brockman and H. Muxfeldt, " A n t i b i o t i c s from Actinomycetes XL Actinomycin 19: C o n s t i t u t i o n and Synthes is of t h e Actinomycin Chromophore ,It Chem. B e r . 91, 1242-83 (1958).

. L

, , I : .."L 13) A.B. Mauger and R. Wade, "The Synthes is of Actinomycin Analogues, P a r t I. 3-Benzyloxy-4-methyl-2-nitrobenzoyl-L-~ t h reon ine and Rela ted Compounds," J. Chem. SOC., 3126- 3132 (May, 1965).

' \

14) V. B e t i n a , "Systematic Analysis of A n t i b i o t i c s Using . "Paper Chromatography," J. Chromatog, 15, 379 (1964).

, I

1 4

I

: 17) R. Bennet t and E. Heftmann, J. Chromatoq, 12, 245 (1963).

# ' 18) M. A n w a r , 5. Chem, Educ., 40, .29 (1963). ..

, _ 19) M. Brenner&ahd A, :Niederwieser, Emerient ia , 1 (1961) .

; . 2 0 ) N. Zdllner and G, W o l f r a m , K l i n Wochschr., 40, 1098 * . D

(1962). * i

I

: . I' 'I * '

I

21) T.M. Lees, M . J , Lynch & F.R. Mosher, nContinuous Flaw I

I .

Thin-Layer Chromatography,N J. Chromatoq., 18, 595-598, ' I . (1965). *

* i 22) J.F. Thompson, W.N. Arnold, and C.J. Morris, "A Sens i t ive I Quali ta t ive T e s t for Sulfoxides on Paper Chromatograms, Nature 197, 380-381 (1963).

. . I

, ' I. .

- J : i . 23) A.P. Safronov, "A New Method f o r Detecting Organic Sulf- . , oxides," Zh. Ana l i t : Khim., 18, 548-550 (1963).

-1 'i , 24) J. D e Pascual de Teresa, "The Reaction of Heteropoly A d w i t h Sulfoxides. 11. Phosphomolybdates of Sulfoxides, "

i m , 42, 495-509 (1946). Anales f i s . Qu

' A . . 1 t,, #

1 %

'