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August 6, 1948
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RI NTLY PUBLISHED RESEARCH CF THE ALL-UNION CHELaC0- P1W &CtlL06ICAL SC37NTD'IC RESEARCH INSTITSE USSR eCbsaiatry of Aydrosyfuohsoneas I. Eupittono and Rubro pI0ms " I. !a. Fbatoveddy, A.N. Eydlln. All-Union Chem harm Soi Res last, Svw&ovek eZhua Obahah iim" Vol 36, 1946, pp 2043-52 K ,w syntheses of eupittone (3,3',Y',5,5'o`a-hearamethasq- 4,4'?dibydroxyoiuoheone) (I) and rubro eae (3,31,3"- trimethaxy. 1,4 '?di2ydeo3+Psuhaono) (II) are described. Both I and n etimulato blood prodnation in guinea pigs; cinder affect produced by actin. !Cleavage of } oagfnohaoOe," I. Is Pbetovskly, A. N. Eyd1in, A21- tan Chen Pharm Sci Rea Fast, Sverdlovsk "Zb !lbeheh Shia" Vol 16, 1946, pp 2053-64 Since enpittone (I) and rnhropbene (II) have been re- parted as having soar t?beromtlostetic properties, the poceibility of ant's aotl-7ity reaidirig in tr nta of I and n prasepted the etu ly of the cleavage of t? to hoonss uaderr a variety of conditions. Amain (III) me also Included in the at*. Shaking I, II, or III In 5% AaCH >mder about 3C0 a p caste of 0 and deter- aluing the u',.11ioed 0 gage 0-utilisation across rmioh are presented. III is essentially completely cleaved in 32 !somas, II requires 15 bows, chile I is mmcbanged in 15 boas, Siedlar oxidation of bBnsoquinene, tol- ugniavne; and nathoVq dnos a led to caaplation of the reactich vithi,-% 2 hours; FhOH yea mmohaaged in 3 ho=, CLASS yATION }'J:-ZT-IICTI:D CENTRAL INTEL r ~p INFORFIIATi8" 'Ff T COUNTRY USSR SUBJECT Soientif+c Research PLACE ACQUIRED USSR DATE ti'' IIaWCRlIATION 19,45-46 of we 55105 "Stff 111515 sus 0or. TOt UMO*Mt efe so a? L.O.. ft as pl. Y N155t0. M=6 tl1551 US"A" M 551!01051011$ 15 A11e Y/Oft W W tlaN1$OM1W Mff01 tf a1,0*1 R tea. f5;11$t5CB1$p a 1$15 POOl u 55tlW61$5. 500? W-R 15fOtte1100 10*0* 505 15.5050 OI e51 IOfi See ft 5T1FR55 N't11$t0a.:NRN000* Oe 515 0110155 "any. `DATE DISTR. 6 "August 1948 NO. OF PAGES 7 NO. OF ENCLS. (LISTED BELOW) SUPPLEMENT TO REPORT NO. THIS IS UNEVALUATED INFORMATION FOR THE RESEARCH USE OF TRAINED INTELLIGENCE ANALYSTS Spin Docomentory as indicated. (Infornation specifically NAVY as . . -1- CLASSIFICATION PICM z Z OuSnu)aunON RESTRICTED Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 I. Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 l Rotative stability of the iB6a0 derivatives to oleavs?eT Derivativee,e G. A. Qarkuahaa A11-won Chem Phaam Rea crude msoadie acid; further-llltration and oooiiig gave "Zhur Obehch ?wdm" Vol 16, 1946, pp 2025 decolorization with biealtite gave 2-iodo-3-hydroo4, gave what appeared to be bsnaoxy-l,4-pyrone. Pyrone was from EtOA to give 3-ttvdroi~-1,4-Phone; it melts at of its !V -Substituted Derivatives of the Alkyl Carbwg1tc- "Zhur 0bahch Khim" Vol 16, 1946, pp 1933-40 toward pnemeon?a and dyaentery approximately equivalent derivative howed some activity toward dysentery, but had dine nucleus. None of the produote showed appreciable properties indicate a pyridonimiae strrctura, i.e., the derivatives were prepared by condeneation of Na aulAspyr- at physiological pA level., a number of carboxylic acid Available evidence for the "normal" and the 2-pyridoni- butylandno) Quinoline," Y. V. Rubtsov, M. V. Lt unova, "Zhur Obehch Min" Vol 16, 1946, pp 1873-6 RESTRICTED RESTRICTED Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 with oo2lectiom or the diatflUtee; the sublimed pc14d, Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 f RESTRKTEP Two methods are explored for the synthesis of the 4Piso?- mer of plawooohin. Syntheses procedures starting with 6- methosy-4?ehloroqutinaaine-1C1 and with 6-meth - q tnoline are, described. tomes of too.wevea is fuehso ee attributed to the forma, tion of an intermediate samiftwhoom. Possibility of a ev m niaction between the reduction-oxidation potential and biological activity corroborated by the finding that the fueheones studied have the same ability to promote hamo- gllobin production in guinea pigs. the quinone series, the potentials are progressively, shifted to more negative values. Velma are given at 250 in the absence of Etas and at 600 after addition of 30 aeigme4 Ball? Fuheones produced two waves, values of which are given at 600 in the pdresence of 30 voles of Et(L Padn- phenoass and ftobsonss, Lie Me, and two Me0 groups (1n 2 sitions) give almost no potential variations. In toted Qttinonee, Thence.., and Fuobeonee," A. G. uSteombng, L. H. Rayne, All-IDodon Chem Therm Rea' Inst, Sveerdlovsk "Zhur ataboh Dim" Vol 16, 1946, pp lI31-42 "Pblarigraphio Study of the Hell-Weve Potentials of Substi- "Alkaloids of Tsachalanthue Norolkovis M. Structure of Tina , the Amino Alcohol Porwed in the F4- dmlrsie of the Alkaloid ':raolulasYthamine," G. P. Men,- "ZMar Crmbcb Ebim" Vol 26, 1946, pp 1311-16 similar to heliotridane, and that the difference in the cawzoe of the Bofeenn degradation is the two cases 10 due to . Since the ?grorop is primar9 In Saes a base, , identical with Prelog'a pyrroliaiaine. It is cowl=d= t peeudchelletridans (source of trap- holantham1o"no)?has the structure of 1-matbYlpy aMm, facidation of traohelanthaeddine with CrO. in dilute H2A04 Sava an amino acid, C , which ar sus as a saoaohydrate. DeearbCV3 t an by means of Ca0 hydrate Results o' vapor oonposi+ion and dateraination of sixtures of beams and CIZ:l3 are gins in tabula.* form at 25.050, 34.6x, a4 44.550. CNunges of free energy and entropy are P. MOM, All-Odon Chem Pharm ass Inst, mown. "9 Mahah Ihiae Vol 16, 194.6, pp 972-82 argy and Entropy of Their formation," $. A. iiteyeu-, I. "het~slmtion of Pressure and Composition of Vapor 111w- tures of Hansen. With Cblorofosm and Changes of Free M%- RESTRICT ED Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 RESTRICTED RESTRICTr 'Neutral Eaters of Sulftnic Acid and Ia01yatomic Alcohols,* U. Na. Ereft, All-IImism Chem HUM Res Thatt Moscoe 'Zhtn Mahoh Ehim" Vol 16, 1946, PP 677-d4 Neutral esters of HI30 and polyatomic alcohols may be prep red by the reae of chiorocarbonate eaters on acid U230L eaters. Most readily preparable and most stable are tt~aa~~ eaters rdroae P-C atom does not have an H atom. Prep. aration of derivatives of an alcohol with a secondary CH (glynerol) failed. Syntheses prooederos described. *Sesltanilamide Derivatives of Aromatic Arsonic Acid: I. Selfaniludde Compounds of Para dnobenseneareonic Acid,' S. V. Vasiloyev, All-Uoion Chem Pharm Roe Inat, Moscow 'Zhur Cbsboh Mdm* Vol 16, 1946, pp /.51-4 Na Neste in water was treated with para-AcNAO6H00 l to yield, on oeoling and partial concentration, pare-(N4- *eetyi(snltanilauaido - acid. The As oopetnd was l by with lit1 to yield pare-eulfanil- ansidobe areenie acid I) the constants of which ere not, given. I in %Q and 3 N NCS was treated with Na2S204 to yield 4,4'-disuTTfanilemidoeremwbensone. Howeverwhen ; the reduet4on was performed by 802 in MOM solution toe= obttainsd4/ -(parrs-aroeaosopheny+l) sulfanilamide. The acid was Inactive against spirochetes or trypanosomes, while the last taro ocmpoucde were 24 times less active than nmvar- semoi. *Allewiao Ee+,ars of T iao-l-Naphthoic Acid;' 3. S. -%W94evekaya, A. A. 3ropechevat, All-Union Chen Mere Fes last, Moscow 'Zhur Cbsheb Pmts' Vol 15, 1945, pp 996-1000 Fo31owiag nw altaedac esters were prepared, all of which were found to have definite anesthetic properties. Et Pet a~aphtr+aoate (I), Me~ pOH, Na, and abaroluto Um were boated; after removal of the LtOH and aaovaos smash alcohol in waouo, the residu? ins poured Into water and mtracted with 0 m o f to the dried extract ga gave ar-%4-snie -l-ne Toasts-2 l1. Treatment of the subject acid, NQI, ItCE, cad C 6H~0 by heating tc Lot tom, filtering, and oonceutra it ohs fo lowed by solutica in ab- solute XI sod addition of alcoholic HGL, gave 3-dlethyrl- asfnoprap,'J. 1-naphthoate-2}C3.. I eel tswatsd with 4-diatby'lemino 1-butanol and Na, and the mixtwee es heated on an oil loath, after which the excess swiss Wankel is removed in iacuo and the reddws poured in Sister and extracted with M20. Treatment of the ex- tract with O-U01 gain 4-die bylamivobutyl tetrab7dro- ~ tboete-2hC1. I, Na, 3't0&, and 1-'iet3>yl- satm-3-bntonol heated an an oil bath, and treated an ab , gwe 3-diutbyiamiao l aeElylprolgl ~r-.6 -4- IMS RICT1SG RESTRICT STAT Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 RESRi m rat contain aaete mat ion of Quinine Alinloide ftich a Nethoaygl Oro in a Matte of Quinine ii woii,e N. Z. Z eon, A. t. 8in*loov3kaya, 111-B on Cbaa There Inst, Noscoc Win" Vol 15, 1945, pp 957-61 fslfoh 6hia" Vol 16, 1946, pp 1077-d6 ditlon of WI. tba aria WAD aotoraotOC wawa M20, xxvm ' ? brae were obtained ceverel oompawda, all of ehioh anco. 1)-Pa~oPlonia said. It wsa ebowes.het two of the oompowide were iaeividusicon- pWMU, while the third we. a mixt we of the two. Siailar Con9enastion in Oft led to a aiwtura of the above cub- stanoei. the produste are separated by orystellim tion from IW and identified as: 6 1,2,3,4 'tetr 7(er 8)-oaphtba7IpropiowdC acid (1) and the 8(or 7)-ndpia t c t iaoro (111. 1 fares an cmdme which neelte at, a hi~hear teaperatmr than the oxiae of U. Clemuneen re- &wtdoe- of I pave the corresponding, butyric acid, which net heating with P205 in PbNe, gsee 1,2,3,4,5,6,7,6-oCta- dmoeQ with aaelgemsted r thr are t e d hstoe oo~yp eoaa an in Wi-P6No to anthreno (Us). OZeaoenea redrootion of n nave the Corr responding bctrio aold, which an cio3iuatIon with P205 in WIG FAb, gate an ir!ser of the M .V dexivh- ative reared dth e-1gemsted Zn to III, ttma she ing that and w we 7- and Eriseaers. hmther iseatmeet of I is dese 4W in the grepsration of the lac one of r - (6-otbaaq .1,2,3,b-~ D1). mo ybutyeia actor n, i. It. Fsdaeow, A121 or Chen Thar lest, Noacow ?Zbwr Obrbeb Rhin" Vol 15, 1945, PP 96" to1loidn proo,dme recd: diluted magi, and the tolme were d wigom&V stirred can d;A treated with ooma:atratw RAIft and tbG ; the reaction arse um then dilated, fii- washed, bmd nepraaipitnted from alkaline solution by Wi or %#4:%. %WO, 2,4?C]23619te, IbO2 cad oaswreial RESTRKTED Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 Sanitized Copy Approved for Release 2011/0/6/29: CIA-RDP80-00809A000600200218-9 d concentrated HZ90 gave 2,4-dicblorobensoia acid. 02$04 a-o2~lc wit neaa MnOg and commercial trated $2004 gars 2-ohioro-4-nitsobensoic acid. Treat nt r4th peya-nitrotolweme gave per -nitrobemsoic acid. eT -1(and 2)T6ionaphtboic Acids and Their De- rivativwa," S. I. , 8. G. ISkhem>dna, All- !eparation of subject acids and their exters described, Peters Include It, N. 2-chloroethyl, 3-chloroY PyL, est4ms, 2-distbylaminc;sth2+1 aster-901, and 3-diet yl- amincpaop l aster-ML Th eioal properties are given. The alumina eaters are not effective . "Zhnr Obaboh Shim" Vol 15, 1945, pp 98?-95 'T*txsb7ftti-~1-(and 2)-Naphthoic Acids and Their Dex v- stivee,w S. I. , H. G. Nlkhank+++?, All- on Chem Phara Inat, Moscow "Zhur Obehoh Rhin" Vol 15, 1945, pp 940-6 Syntheses for the preparation of subject acids and their derivatives from ar-l-Aminotetralin end 15;1 described. Phfei al properties are also given. "Alkaloids of Cacalla Hastata," V. S. Honrovalbv, gem'ehilcov, All-Union Chem Thins Res,Inat, Moscow 'Z6ta Obaboh Shim" Vol 15, 1945, pp 328-31 tbo udit wetted bW 10% W QH and extracted with C2H4C12i extract as earEreoted with % 8280G1, __and the latter aaee alkaline with 25%1Q9g0H and ewtracted with CH015. After The sib leAd is h drol red by boilii in 7% alooiolio ICs to yield a dibasic H0 acid, C8H13W-(C02H)2, *doh ma a awed bsstanseinio acid, and an amino glyool, 01.51, deieb as named hastanecias. The alk0oid possesses ex- "Ar+eoolins N-axida (Cwmreoollne) 3" U. N. Mcbikina, A. Ya. Barlin, S? D. Oasanova, IV -Obion Chem Ram Piss That, B%% awtriniag 0. Q5 atom of active D. ?!h-+ ntxw s is*, tbst satod with Fleric acid and allowed to stand, to rent with ssttaatod . The 0 eatrsot of the wlx- "Zhta; Pritlad Rhin" Vol 18, 1945, pp 634-7 -6- RBSTRICYIO? RESTRICTED Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9 if RESTRICTED yiem exe?ellme /V/ -=we pdrate. The mete .as' further UwW with Wi zad several por bone of CM-1 to yield areoollu. N-*dde-El. Trsatne nt of thin th 1C gene the rue bees as a ?ellawiak oil.tewemt of the El mat with sag in water on areeol1ne anifesate 99 d ausGes. The gather tiger ooataied ersooliae % nas isolated as the oxalate. The 9ndioatlons are the 8 .Rests the emotion of the oxide to the free bees, thm nplfedo eater beisg as laet.rmsdlate. the *aOO ass awwwad In xaona, and the residue was cooled ~ep.d tre*t.d with ocudentnted M M. The pe?.eipitated 1 1e is0oa8,004 fIlt red off,' eeesbed, and dried$ with oMmuWated M. folinwing by eehing with VajpN weep the I l salt. The El salt is um b - ted in the preeaee of ltenW ltl to, yield dil~~rlrol~ 9ra.~y- ePlteap.ration of From Tbebaim,e 1. Eh. Fe1 *deran, A. I: I rb~g, on M > am not, swam 5Zha Prlklsd lpeise Vol 18, 194, pp ?15-1? W NW= wee treated with ?s stirred = U solution and the Me rented with H2GG. liset of RESTRICTED STAT. 0 Sanitized Copy Approved for Release 2011/06/29: CIA-RDP80-00809A000600200218-9