Abstract
The synthesis of pyrrolo[2,3-d]pyrimidine derivatives by direct aminocarbonylation was demonstrated using solid Co2(CO)8 as a CO source in an autoclave at elevated temperature by reacting an aryl halide scaffold with a variety of amines. Using this method, 12 non-glutamate-type pyrrolo[2,3-d]pyrimidine analogues were prepared. Some compounds exhibited antibacterial activity against both Gram-positive and Gram-negative bacteria.
References
1.
Berman E.M.
, and
Werbel L.M.
, J. Med. Chem. , 1991 , 34 , 479 .
2.
Supuran C.T.
,
Scozzafava A.
,
Jurca B.C.
, and
Iiies M.A.
, Eur. J. Med. Chem. , 1998 , 3 , 83 .
3.
Guo X.
,
Li Y.
,
Tao L.
,
Wang Q.
,
Wang S.
,
Hu W.
,
Pan Z.
,
Yang Q.
,
Cui Y.
,
Ge Z.
,
Dong L.
,
Yu X.
,
An H.
,
Song C.
, and
Chang J.
, Bioorg. Med. Chem. Lett. , 2011 , 22 , 6770 .
4.
Varaprasad C.V.
,
Ramasamy K.S.
,
Girardet J.L.
,
Gunic E.
,
Lai V.
,
Zhong W.
,
An H.
, and
Hong Z.
, Bioorg. Chem. , 2007 , 35 , 25 .
5.
Mohamed M.S.
,
Rashad A.E.
,
Adbel-onem M.
, and
Fatahalla S.S.
, Z. Naturforsch. C , 2007 , 62 , 27 .
6.
Nagashima S.
,
Hondo T.
,
Nagata H.
,
Ogiyama T.
,
Maeda J.
,
Hoshii H.
,
Kontani T.
,
Kuromitsu S.
,
Ohga K.
,
Orita M.
,
Ohno K.
,
Moritomo A.
,
Shiozuka K.
,
Furutani M.
,
Takeuchi M.
,
Ohta M.
, and
Tsukamoto S.
, Bioorg. Med. Chem. , 2009 , 17 , 6926 .
7.
Jung M.H.
,
Kim H.
,
Choi W.K.
,
El-Gamal M.I.
,
Park J.H.
,
Yoo K.H.
,
Sim T.B.
,
Lee S.H.
,
Baek D.
,
Hah J.M.
,
Cho J.H.
, and
Oh C.H.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 6538 .
8.
Asukai Y.
,
Valladares A.
,
Camps C.
,
Wood E.
,
Taipale K.
,
Arellano J.
,
Cassinello A.
,
Sacristán J.A.
, and
Dilla T.
, BMC Cancer , 2010 , 10 , 26 .
9.
McHardy T.
,
Caldwell J.J.
,
Cheung K.M.
,
Hunter L.J.
,
Taylor K.
,
Rowlands M.
,
Ruddle R.
,
Henley A.
,
de-HavenBrandon A.
,
Valenti M.
,
Davies T.G.
,
Fazal L.
,
Seavers L.
,
Raynaud F.I.
,
Eccles S.A.
,
Aherne G.W.
,
Garrett M.D.
, and
Collins I.
, J. Med. Chem. , 2010 , 53 , 2239 .
10.
Hilmy K.M.H.
,
Khalifa M.M.A.
,
Hawata M.A.A.
,
Keshk R.M.A.
, and
El-Torgman A.A.
, Eur. J. Med. Chem. , 2010 , 45 , 5243 .
11.
Suster D.C.
,
Tarnauceanu E.
,
Ionescu D.
,
Dobre V.
, and
Niculescu-Duvaz I.
, J. Med. Chem. , 1978 , 21 , 1162 .
12.
John W.
,
Picus J.
,
Blanke C.D.
,
Clark J.W.
,
Schulman L.N.
,
Rowinsky E.K.
,
Thornton D.E.
, and
Loehrer P.J.
, Cancer , 2000 , 88 , 1807 .
13.
Taylor E.C.
, and
Liu B.
, J. Org. Chem. , 2003 , 68 , 9938 .
14.
Taylor E.C.
,
Kuhnt D.
,
Shih C.
,
Rinzel S.M.
,
Grindey G.B.
,
Barredo J.
,
Jannatipour M.
, and
Moran R.G.
, J. Med. Chem. , 1992 , 35 , 4450 .
15.
Smith H.O.
,
Blessing J.A.
, and
Vaccarello L.
, Gynecol. Oncol. , 2002 , 84 , 140 .
16.
Grant S.C.
,
Kris M.G.
,
Young C.W.
, and
Sirotnak F.M.
, Cancer Invest. , 1993 , 11 , 36 .
17.
Roberts J.D.
,
Poplin E.A.
,
Tombes M.B.
,
Kyle B.
,
Spicer D.V.
,
Grant S.
,
Synold T.
, and
Moran R.
, Cancer Chemother. Pharmacol. , 2000 , 45 , 103 .
18.
Gangjee A.
,
Yu J.
,
Kisliuk R.L.
,
Haile W.H.
,
Sobrero G.
, and
McGuire J.J.
, J. Med. Chem. , 2003 , 46 , 591 .
19.
Shohreh M.
,
Falcón-Pérez J.M.
,
González E.
,
Millet O.
,
Mato J.M.
, and
Farzad K.
, Chem. Pharm. Bull. , 2012 , 60 , 70 .
20.
Itoh F.
,
Yoshioka Y.
,
Yukishige K.
,
Yoshida S.
,
Wajima M.
,
Ootsu K.
, and
Akimoto H.
, Chem. Pharm. Bull. , 1996 , 44 , 1498 .
21.
Itoh F.
,
Yukishige K.
,
Wajima M.
,
Ootsu K.
, and
Akimoto H.
, Chem. Pharm. Bull. , 1995 , 43 , 230 .
22.
Itoh F.
,
Yoshioka Y.
,
Yukishige K.
,
Yoshida S.
,
Ootsu K.
, and
Akimoto H.
, Chem. Pharm. Bull. , 2000 , 48 , 1270 .
23.
Barnett C.J.
,
Wilson T.M.
, and
Kobierski M.E.
, Org. Process Res. Dev. , 1999 , 3 , 184 .
24.
Baburajan P.
,
Senthilkumaran R.
, and
Elango K.P
, New. J. Chem. , 2013 , 37 , 3050 .
25.
Baburajan P.
, and
Elango K.P.
, Tetrahedron Lett. , 2014 , 55 , 1006 .
