R
SYNTHETIC COMMUNICATIONSV
7
[4] (a) Li, J.; Sun, M.; He, G.; Xu, X. Ultrason.Sonochem. 2011, 18, 412–414.; (b) Li, J.; Dai,
H.; Xu, W.; Li, T. An Efficient and Practical Synthesis of Bis(indolyl)Methanes Catalyzed
by Aminosulfonic Acid under Ultrasound. Ultrason.Sonochem. 2006, 13, 24–27.
[5] (a) Zahran, M.; Abdin, Y.; Salama, H. ARKIVOC. 2008, 11, 256–265.; (b) Pal, R. IOSR J.
Appl. Chem. 2013, 3, 1–8.
ꢀ
ꢀ
ꢀ
[6] Penieres-Carrillo, G.; Garcıa-Estrada, J. G.; Gutierrez-Ramırez, J. L.; Alvarez-Toledano, C.
Infrared-Assisted Eco-Friendly Selective Synthesis of Diindolylmethanes. Green Chem.
2003, 5, 337–339.
[7] Ye, L.; Cai, S.-H.; Wang, D.-X.; Wang, Y.-Q.; Lai, L.-J.; Feng, C.; Loh, T.-P. Photoredox
Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond
Cleavage. Org. Lett. 2017, 19, 6164–6167.
[8] (a) Stolle, A.; Szuppa, T.; Leonhardt, S. E. S.; Ondruschka, B. Chem. Soc. Rev. 2011, 40,
2317–2329.; (b) M’hamed, M. O. Synth. Commun. 2015, 45, 2511–2528.; (c) Ranu, B. C.;
Chatterjee, T.; Mukherjee, N. 2015, RSC Green Chemistry, Ball Milling Towards Green
Synthesis: Applications, Projects, Challenges; B. Ranu, A. Stolle, eds.; Royal Society of
Chemistry.
[9] (a) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110,
2250–2293.; (b) Sundberg, R. J. The Chemistry of Indoles, AcademicPress, New York,
1996.; (c) Brown, R. K., Indoles Part I; Houlihan, W. Ed.; Wiley-Interscience: New York,
1972; pp 385.; (d) Casapullo, A.; Bifulco, A. G.; Bruno, I.; Riccio, R. J. Nat. Prod. 2000,
63, 447–451.; (e) Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.;
Yukawa, H. J. Nat. Prod. 2000, 63, 596–598.; (f) Bao, B.; Sun, Q.; Yao, X.; Hong, J.; Lee,
C. O.; Sim, C. J.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2005, 68, 711–715.; (g) Ertl, P.; Jelfs,
S.; Mu€hlbacher, J.; Schuffenhauer, A.; Selzer, P. J. Med. Chem. 2006, 49, 4568–4573.
[10] (a) Praveen, P. J.; Parameswaran, P. S.; Majik, M. S. Bis(indolyl)Methane Alkaloids:
Isolation, Bioactivity, and Syntheses. Synthesis 2015, 47, 1827–1837.; (b) Kathleen, A.;
Merrill, A. G. PCT. Int. Appl. WO Patent 99; Chem. Abstr. 1999, 130, 276–765.
[11] (a) Ge, X.; Fares, F. A.; Yannai, S. Chem. Abstr. 2000, 73, 462b.; (b) Chang, Y. C.; Riby, J.;
Chang, G. H.; Peng, B. C.; Firestone, G.; Bjeldanes, L. F. Cytostatic and Antiestrogenic
Effects of 2-(Indol-3-Ylmethyl)-3,30-Diindolylmethane, a Major in Vivo Product of Dietary
Indole-3-Carbinol. Biochem. Pharmacol. 1999, 58, 825–834.; (c) Chang, Y. C.; Marques,
M.; Laflamme, L.; Benassou, I.; Cissokho, C.; Guillemette, B.; Gaudreau, L. BMC Cancer.
2014, 14, 524.; (d) Hong, C.; Kim, H. A.; Firestone, G. L.; Bjeldanes, L. F. Carcinogenesis.
2002, 23, 1297–1305.; (e) Shilling, A. D.; Carlson, D. B.; Katchamart, S.; Williams, D.
Toxicol. Appl. Pharmacol. 2001, 170, 191–200.
[12] Staub, R. E.; Onisko, B.; Bjeldanes, L. F. Fate of 3,30-Diindolylmethane in Cultured MCF-7
Human Breast Cancer Cells. Chem. Res. Toxicol. 2006, 19, 436–442.
[13] Khuzhaev, B. U.; Aripova, S. F.; Shakirov, R. S. Arundine — A New Dimeric Alkaloid
from the Roots ofArundo Donax. Chem. Nat. Compd. 1994, 30, 635.
[14] Bell, R.; Carmeli, S.; Sar, N. Vibrindole A, a Metabolite of the Marine Bacterium, Vibrio
Parahaemolyticus, Isolated from the Toxic Mucus of the Boxfish Ostracion Cubicus. J.
Nat. Prod. 1994, 57, 1587–1590.
[15] Osawa, T.; Namiki, M. Structure Elucidation of Streptindole, a Novel Genotoxic
Metabolite Isolated from Intestinal Bacteria. Tetrahedron Lett. 1983, 24, 4719–4722.
[16] Cai, S. X.; Li, D. H.; Zhu, T. J.; Wang, F. P.; Xiao, X.; Gu, Q. Q. Two New Indole
Alkaloids from the Marine-Derived Bacterium Aeromonas sp. CB101. Hca. 2010, 93,
791–795.
€
[17] Veluri, R.; Oka, I.; Wagner-Dobler, I.; Laatsch, H. New Indole Alkaloids from the North
Sea Bacterium Vibrio Parahaemolyticus Bio249. J. Nat. Prod. 2003, 66, 1520–1523.
[18] Kobayashi, M.; Aoki, S.; Gato, K.; Matsunami, K.; Kurosu, M.; Kitagawa, I. Marine
Natural Products. XXXIV. Trisindoline, a New Antibiotic Indole Trimer, Produced by a
Bacterium of Vibrio sp. separated from the Marine Sponge Hyrtios Altum. Chem. Pharm.
Bull. 1994, 42, 2449–2451.