The preparation of iodine‐containing x‐ray contrast substances. III. The structure of “choloselectan”

Abstract

Clioloselectnn, n re]iiitccl S-ruv coiitrust for tlic pill blncl~ler. is atatcd to pos..cas foniiu~ii (I). I t nlq&irs to Irnvc ~l e r i~ 1ircpwerI IIV tIio roil~Ieiientiori of ioc~oisntin (11) wit~i 3 : ~-c~i-iirc~o-~-~-~igc~rosgeilic~sgiic~eto-pliciioiio (HI), nncl nltlioigli the ~~roiliict frorii this rciiction w i i H piveil atriictum (I\'), it is itow sliow~i tlint I lie oiilv inolitblc clietiiir~il iiiiliviiliinl is tho siiiiplu hrivtitiw (V), tIic Iiydrvsgut\;yl proiip being eIiiiiiiii~tci~ by ligclrolgsis rlitritig tliu i~oiiilci~aiitiori. Cl~oloselr~~trin WIIS ~~rob;ibIy tlic c a n i~~~t t~i~I (V) iii II wry iriipiiru I I~I I I~.Cliolosclcctrin, ii rcputerl .Y-r:iy ctiiitriist. for the g~ill l)liitltler, w t s first mciit.ioiic!cl 11y l'ril)rmi.* It wis stater1 to IJC t lie iotliniitetl 3-~~1ienylquititrlittc-~I-c~iirlrosylic iicitl deriviitivc (I), i t n i l II further reference to the cotnpotititl w i s rtintlc hy lIiiix,z hut since then Choloselcctiin liiis only liccri inrtitionctl Iwicfly Iiy I<leil)cr,:l \vho repnrteil tlittt nltliouglt it gave exccllent S-my pictures it iviis not. ititrotlucctl ou techuiciil groiiritls. Ilttrinpts to obtain ii spritncji of Cliolosclectiin were uumccewftil. C0.Hco .(I\') (v) 0.J) Bcfore tlie ~~iil~licntiori of tlie piper hy Kleiber, itntl the iippcnriiuce of the preliniiniiry reports on I~iliselecttiti (see previous pnpcr), work Iiiid Itreti bcgiiii on the syntlicsis of the niolecnle (I) ~-1iicli is nu Atopliiin clcririitive, r~t r t l vie itre nox nhlc to t.lirow sonic light on the supposrd structure of Cholosclcctnu.Tlic fiict tlirit C'holosclrctnn WIIR originiilly givrii forniuln (1) suggestetl tltiit it WS inn& by tlic courlcnsntion of d-iotloisiitiii (I I ) with 3 : 6-tli-iotlo-~i-Itytlrosy-2-~-liytlrosyetIiylittrt~to~1lir1iorte i n presence of strong ulkiili uittler tltc conditions of the Pfitxingcr retiction.* This :icetophetione tlerivutirc is, Itowever, not tlcscril)ctl in tlie literature iiud severtil tiitsuccessfi~l iittcnipts to syntltcsi~c the conipoutid showctl tlint, it woultl lic tin estrrnicly clifiicrtlL nioleculc to prepiire. Tlic isonicric rJ-liytlrosyetltyl ether of 3 : B-tli-iotlo-.l-Iiytlrooxyiicetoplieuonc (I1 I) is, however, tlcscril)ctl i n n Sclicring-Knlil- ltcrs w i t h iotloisiitiu to giveAtopliun tlerivutivcs for use [is gull bliitltlcr S-riiy coutnists. This secotid putent describes in piirticiilnr tlcttiil the contleiisiition of 5-iodoimtin (11) with (I1 I) iiiid tlie renitirknblc cliiini is innilc thtit the Iiydroxyethyl group tiiigrtites cluring the rcnction froiii the phenolic oxygen ntoni to position 3 of tlio quirioliiic ~tucleus to give the nioleculc (1 V). Tliis rnigriitioii, wlticli nppeiirs to he quite outside the experience of orgiinir clirniistry, wiis supported by the eypthexis of (11') from 5-ioiloiutitin uiid 3 : B-tli-iotlo-J-hydrosy-yhydroxyhutyro~~lieiioiit~, 1)ut the iticiitity of the two products, which melt with tlcconipositiou at high tcnipcmtores, wns deduced solely %on1 the siiniliirity of their tIccotupositio...

Evaluation of Toxicity of Phenolic Compounds Using &lt;i&gt;Aedes aegypti&lt;/i&gt; (Diptera: Culicidae) and &lt;i&gt;Artemia salina&lt;/i&gt;

“…[10] mp 173˚C); 1H and 13C NMR, IR and LRMS data obtained for compound 2b are in agreement with those in the literature [9] [10].…”

“…In the present study it was used as positive control. The results indicate the same confidence interval for both LC 10 . The value of LC 10 is close to the value expected for the WHO-World Health Organization CD.…”

“…A comparison of the results of the phenolic compounds with and without the addition of Tween 80 ® shows a difference in the LC 10 , thus increasing the toxicity and/or larvicidal potential (see Table 1 and Table 2). However, the compound 2,6-diiodophenol showed a slight increase in lethal concentrations.…”