300071; 3. , ) E2m ail: 263. net CH EM ICAL JOU RNAL O F CH IN ESE UN IV ERS IT IES CH 2CO 2H N H H N
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1 V o l. 2 o C EM ICAL JU RAL C I ESE U IV ERS IT IES , 2,, 2, (., 00072; 2.,, 0007;., 006) DCC ( ) gb t (2 ), , 52% 8%. M R, P M R, IR ,., L 260 BEL ; ; ; 626 A (2002) [ ] (PA s), [2, ]..,,, [4 ]., Α2, [5 8 ],. 52 (52 luo rou racil) [9 ],,., [0 2 ],, (T egfu r).,,,, 52 22,, [ ]., [4 6 ] ,. : B rc 2C K g 2 2 C 2C C 2C 2 4 C 2C 2 () DCCgDM ()DCCgDM,B t (B t ) (2) 2C 2C 2Et (2) 2C (R ) P ( Ph) 2 (5) C 2C C 2C 2E t C 2C C 2C C P ( Ph) 2 2 mo lgl a R: 6a. ; 6b. C ; 6c. Bu; 6d. C 2Ph; 6e. C 6 5; 6f. 2, 42D ich lo ro C6 ; 6g. 42C l C 6 4; 6h. 2 2 C6 4; 6i C6 4; 6j. 42M e C 6 4; 6k. 22M e C6 4; 6l. 42M e C 6 4; 6m. 42C l C6 4; 6n., 42C 2 C6. 6 R : : ( : ). : (96 ),,, W ittig. E2m ail: liuxuejun89@ 26. net
2 00 V o l. 2 B ruker A C2P200 M R (TM S P 4 ), Yanaco C Co rder M T, ico let 5DX IR. ( Λm, ), DM 4A, CC l P 2 5.,.. Α- (5) Α2 [ 7, 8 ] (2) 0 mmo l g (. 5 mmo l) K 20 ml. 40, g (45 mmo l) 0 ml, 0 m in., C l p 5. 5, 2 h. 6 h. 2 89% ; m. p.,,. > 270 ; 2 h,,, p 2, M R, : 4. 4 (s, 2 ), (d,, J CC = 7. 6 z),. 54 (s, b r, ) ; (% ) : C 8. 49, 2. 75, ( % : C 8., 2. 68, 4. 89).. Α- (5- -- ) () 5 mmo l mmo l 2 00 ml, 25 ml DM, g (5. 5 mmo l)dcc DM 0 ml, 40 m in., 2 h, 5 mmo l,., DM (5 ml ),,,,, g ( 20 ),. 2, 85% ; m. p. J C= 5. 7 z), (q, 2, ( t,, ; M R, :. 9 (t,, J CC= 7. z), (s, 2 ), (d,, J CC= 7. z),. 86 (d, J CC= 7. 6 z), J C = 5. 7 z),. 54 ( s, b r, ) ; (% ), : C 44. 2, 4. 66, 5. 09; : C 4. 96, 4. 4, Α- (5- -- ) (4) (2 mmo l) Α2(52 22 ) 0 ml 2 mo lgl a, 4 h. p 2, h.,, 45, % ; m. p. 2 ), (d,, > 270 ; J CC = 7. 6 z), (t,, M R, :. 8 (d, 2, J C = 5. 8 z), 4. 8 (s, J C = 5. 8 z),. 8 (s, b r, ) ; (% ), : C 9. 47,. 5, 7. 20; : C 9. 9,. 29, Α- [ (5- -- ) ]-Α- ( ) -, - (6a 6n) mmo l Α2(52 22 ) (4) mmo l 2 00 ml, 5 ml DM, g (. 2 mmo l)dcc DM 0 ml, 40 m in., 2 h, mmo l Α2,., DM (5 ml ).,,,, g ( 20 ), [ 9 ], K, 22.
3 o. 7 : ,,,. 6 M R, IR 2. Α2(52 22 ) Α2(52 22 ), Α ,,,, (2% ). DCCgB t 52 22,,,., DCCgB t Table P M R and M R (DM S, ) of compounds 6 Compd. P M R M R 6a (d, 2, J C= 5. 7 z, C 2) ; 4. 2 (dd., 2, PC 2, 2 J PC= 4. 5 z, J C= 7. 0 z) ; ( s 2, C 2C ) ; (m, 0, 2C6 5) ; 8. 0 (d,, J CC= 7. z, C= C ) ; ( t,, J C= 5. 7 z, C 2) ; (m,, C 2P) ;. 8 (s,, (C ) 2 ). 6b (dd,, C, J CCP= 8. 2 z, J CC= 7. 6 z) ;. 88 (d, 2, J C= 5. 9 z, C 2) ; ( s, 2, C 2C ) ; (m,, PC, ) ; (m, 0, 2C 6 5) ; 8. 0 (d,, C= C, J CC= 7. 0 z) ; 8. 4 (t,, J C= 5. 9 z, C 2) ; (m,, C P) ;. 47 (s,, (C ) 2 ). 6c (t,, C, J CC= 7. 8 z) ; (m, 6, C 2C 2C 2) ;. 89 (d, 2, J C= 5. 8 z, C 2) ; (s, 2, C 2C ), (m,, PC ), (m, 5, 2C6 5) ; (d,, C= C, J CC= 7. z) ; (t,, J C= 5. 8 z, C 2) ; (m,, C P) ;. 7 (s,, (C ) 2 ). 6d (m, 2, C 2Ph) ;. 88 (d, 2, J C= 5. 7 z, C 2) ; 4. 5 (s, 2, C 2C ) ; (m,, PC ) ; (m, 5, C6 5) ; (d,, C= C, J CC= 7. 6 z) ; ( t,, J C= 5. 8 z, C 2) ; (m,, C P) ;. 50 (s,, (C ) 2 ) 6e (d, 2, J C= 5. 9 z, C 2) ; ( s, 2, C 2C ) ; (dd.,, 2 J PC= 2. 0 z, J C= 8. 5 z, PC ) ; (m, 5, C 6 5) ; (d,, C= C, J CC= 7. 6 z) ; (t,, J C = 5. 9 z, C 2) (d,, J C= 8. 5 z, C P). 42 ( s, br,, (C ) 2 ) 6f (d, 2, J C= 5. 9 z, C 2) ; ( s, 2, C 2C ) ; (dd.,, PC, J PC= 24. z, J C= 9. 2 z) ; (m,, (C , 4 2C l2c 6 ) ; 8. 0 (d,, C= C, J CC= 7. 9 z) ; ( t,, J C= 5. 9 z, C 2) ; (d,, J C= 9. 2 z, C P) ;. 49 (s,, (C ) 2 ). 6g (d, 2, J C= 5. 8 z, C 2) ; 4. 5 ( s, 2, C 2C ) ; 5. 9 (dd.,, J PC= 2. 2 z, J C= 8. 5 z, PC ) ; (m, 4, 2C C lc6 4) ; (d,, C= C, J CC= 7. 6 z) ; (t,, J C= 5. 8 z, C 2) ; (d,, J C= 8. 5 z, C P) ;. 58 (s, br,, (C ) 2 ) 6h (d, 2, J C= 5. 8 z, C 2) ; (s, 2, C 2C ) ; (dd.,, PC, J PC= z, J C= 9. 5 z) ; (m, 5, 2 (C C6 4+ C= C ) ; (t,, J C= 5. 8 z, C 2) ; (d, 2, J C= 9. 5 z, C P) ;. 55 (s,, (C ) 2 ) 6i (d, 2, J C= 5. 9 z, C 2) ; ( s, 2, C 2C ) ; 6. 6 (dd.,, J PC= 2. 2 z, J C= 9. z, PC ) ; (m, 5, 2 (C C6 4+ C= C ) ; (t,, J C= 5. 9 z, C 2) ; (d,, J C= 9. z, C P) ;. 49 (s, br,, (C ) 2 ) 6j (s,, C C6 4) ;. 8 (d, 2, J C= 5. 8 z, C 2) ; 4. 9 ( s, 2, C 2C ) ; (dd.,, 2 J PC= 2. 4 z, J C= 9. z, PC ) ; (m, 4, 2C M ec 6 4) ; (d,, C= C, J CC= 7. 6 z) ; ( t,, J C= 5. 8 z, C 2) 9. 5 (d,, J C= 9. z, C P) ;. 40 ( s, br,, (C ) 2 ) 6k (s,, C C 6 4) ;. 89 (d, 2, J C= 5. 8 z, C 2) ; (s, 2, C 2C ) ; 6. 4 (dd.,, PC, 2 J PC= 22. z, J C= 9. 8 z) ; (m, 4, 2C M ec 6 4) ; 8. 0 (d,, C= C, J CC= 7. 5 z) ; ( t,, J C= 5. 8 z, C 2) ; (d,, J C= 9. 8 z, C P). 46 (s,, (C ) 2 ) 6l (s,, C C 6 4) ;. 88 (d, 2, J C= 5. 8 z, C 2) ; (s, 2, C 2C ) ; (dd.,, 2 J PC= 2. 6 z, J C= 9. 9 z, PC ) ; (m, 4, 2C M ec 6 4) ; (d,, C= C, J CC= 7. 6 z) ; 8. 5 ( t,, J C= 5. 8 z, C 2) ; 9. (d,, J C= 9. 9 z, C P) ;. 50 ( s, br,, (C ) 2 ) 6m (d, 2, J C= 5. 8 z, C 2) ; 4. 9 ( s, 2, C 2C ) ; (dd.,, J PC= z, J C= 7. 6 z, PC ) ; (m, 4, 2C C lc6 4) ; 8. 0 (d,, C= C, J CC= 7. 5 z) ; ( t,, J C= 5. 8 z, C 2) ; (d,, J C= 7. 6 z, C P) ;. 4 ( s, br,, (C ) 2 ) 6n (d, 2, J C= 5. 7 z, C 2) ; (s, 2, C 2C ) ; (dd.,, PC, J PC= z, J C= 9. 5 z) ; ( s, 2, C 2 ) ; (m,, 2C6 5+, 42C 2C6 ) ; (d,, C= C, J CC= 7. 4 z) ; ( t,, J C= 5. 7 z, C 2) ; (d,, J C= 9. 5 z, C P) ;. 48 ( s,, (C ) 2 ).
4 02 V o l. 2 Table 2 Exper imen tal data of compounds 6 IR, Μ π gcm - Yield Elem ent analysis o. m. p. g C= P= P C (% ) C,, (calculated, % ) 6a (dec. ) 5. 29,. 90,. 76 (5. 44, 4.,. 42) 6b (dec. ) 52. 2, 4. 25,. 6 (52. 9, 4. 40,. ) 6c (dec. ) , 5., (54. 95, 5. 6, 0. 25) 6d (dec. ) , 4. 40, 9. 6 (57. 9, 4. 5, 9. 65) 6e (dec. ) , 4. 5, (57. 25, 4. 27, 9. 89) 6f (dec. ) 5. 2,. 8, (5. 04,. 49, 8. 82) 6g (dec. ) ,. 68, 9. 0 (5. 97,. 86, 9. 2) 6h (dec. ) ,. 90,. 69 (5. 04,. 79,. 45) 6i (dec. ) 5. 6,. 8,. (5. 04,. 79,. 45) 6j (dec. ) , 4. 8, (57. 9, 4. 5, 9. 65) 6k (dec. ) 56. 4, 4. 0, (56. 8, 4. 9, 9. 9) 6l (dec. ) 56. 4, 4. 54, 9. 0 (56. 8, 4. 9, 9. 9) 6m (dec. ) 5. 85, 4. 07, (5. 97,. 86, 9. 2) 6n (dec. ) , 4. 0, (55. 09,. 96, 9. 8) Α- Α2, (4) (6)., : Α2, Α2, Α2 ;, :.,.,. 2. ( P M R M R ), () P M R ,,. (2) M R, ,., [5 ].,,,,,,., Α2,, Α2,,,,., cm - ; C cm - ; P P C cm cm - ; 6a 6n, c= 0-5 mo lgl, L 260 BEL 7404., (L 260 BEL 7404),. Table The inh ibition rate (% ) of the compounds 6a-n (c= 0-5 molgl ) on cell line (L -60 and BEL 7404) Compound 6a 6b 6c 6d 6e 6f 6g 6h 6i 6j 6k 6l 6m 6n L BEL [ ] ielsen P. E., Egho lm M., Berg R.. et a l.. Science[J ], 99, 254: [ 2 ] ielsen P. E., aimm a G.. Chem. Soc. Rev. [J ], 997, 26 (2) : 7 78 [ ] Carlsson C., Jonsson M., o rden B. et a l.. ature[j ], 996, 80: 207 [ 4 ] ZA Yu2en ( ), ZA Guo2 ui( ). E lem ental rganic Chem istry ( ) [M ], Beijing: T sighua U ni2 versity P ress, 998
5 o. 7 : [ 5 ] Klenner T., V alenzuele2paz P., Kepp ler B. K. et a l.. Cancer T reaṫ Rev. [J ], 990, 7 (22) : [ 6 ] A therton. R., assall C.., L am bert R. W.. J. M ed. Chem. [J ], 986, 29 () : [ 7 ] Cassaigne A., L aco ste A. M., euzil E.. A ctual Ch im. T heṙ [J ], 980, 7: 8 22 [ 8 ] LU ai2yan, ZA G an2j ing, C E X in et a l.. Synthetic Comm un. [J ], 998, 28 (0) : [ 9 ] D ush indky R., P leven E., eidelberger C.. J. Am. Chem. Soc. [J ], 957, 79: [ 0 ] WA G Yan2Guang ( ), C E Yao2Zu ( ), X IA X in2l iang ( ) et al.. Chem. J. Ch inese U niversities( ) [J ], 995, 6 (6) : [ ] WA G Yan2Guang ( ), T IA Xuan ( ), L I J ing2x in ( ) et al.. Chem. J. Ch inese U niversities( ) [J ], 99, 4 (0) : [ 2 ] M enger. M., Rourk M. J.. J. rg. Chem. [J ], 997, 62 (26) : [ ] Sem ko T. V., Burov S. V., V lasov G. P.. Edited by Ram age R., Ep ton, R.. Pep ṫ 996, P roc. Euṙ Pep ṫ Symp. 24th [C ], Kingw info rd, U K: M ayflow er Scientific, 996 (pub. 998) : [ 4 ] L IU Xue2Jun, C E Ru2Yu.. Ch inese Chem. L etṫ [J ], 999, 0 (9) : [ 5 ] L IU Xue2Jun, C E Ru2Yu, W E G L in ong et a l.. eteroatom Chem istry[j ], 2000, (6) : [ 6 ] XU E2Jun L iu, RU 2Yu Chen.. Pho spho rus Sulfur Silicon and Relative E lem ent[j ], 200, 76: 0 [ 7 ] lek syszyn J., Subo tkow ska L., M astalerz P.. Synthesis[J ], 979, (2) : [ 8 ] Yuan C. Y., W ang G. K., Chen S. J.. Synthesis[J ], 990, (6) : [ 9 ] Ko synk ina L., W ang G. K., Chyan L iang T.. T etrahedron L etṫ [J ], 994, 5 (29) : Syn thes is and An ticancer Activ ities of ovel 5-luorourac il--yl Phosphonotr ipeptides L IU Xue2Jun, 2,, C E R u2yu 2, YA G Yuan2Yuan (. S chool of Chem ical E ng ineering, T ianj in U niversity, T ianj in 00072; 2. Institu te and ational K ey L aboratory of E lem ento2 rg anic Chem istry, ankai U niversity, T ianj in 0007;. B ase f or P ostd octoral S cientif ic R esearch ing of T ianj in P harm aceu tical Incoṙ L td. T ianj in 006, Ch ina) Abstract A series of novel 52fluo rou racil22yl pho sphono tripetides w ere syn thesized in yield 52% 8% by pep tide coup ling reaction w ith DCCgB t as the activiating carboxyl group reagen ṫ A ll p roducts w ere characterized by M R, P M R, IR spectra and elem en tal analyses. T he facile m ethod w as u sed to syn thesize 52fluo rou racil22yl acetic acid (an impo rtan t in term ediate ). It w as found tha t tw o m a in facto rs affected the conversion of [ ( 52fluo rou racil22yl ) m ethylfo rm yl ] am inom ethylfo rm ic acid to the t it le com pound s. ne is the app a ren t steric h ind rance of an Α2a ryl group having a bu lky sub stituen t at the o rtho2po sition. A no ther is the electron ic effect of the sub2 stituen t of the Α2aryl group s. T he electron2w ithdraw ing group s decrease the nucleoph ilicity of the am ino group. T he yields of all p roducts con tain ing the strong electron2w ithdraw ing group s w ere low er than tho se of o ther p roducts. T he in vitro an titumo r activity test show ed that som e of the syn thesized compounds are the po ten tial an ticancer agen ṫ Keywords 52 luo rou racil; Pep tide coup ling; Pho sphono tripep tides; A n ticancer activity (Ed. : J, Z)
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Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering,
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