174531-85-2Relevant academic research and scientific papers
Synthesis of the Antitumor Antibiotic LL-C10037α
Wipf, Peter,Kim, Yuntae
, p. 3518 - 3519 (1994)
(+/-)-LL-C10037α and its C(4)-epimer were prepared in nine steps from 2,5-dimethoxyaniline.The concise synthetic route represents the first synthesis of this highly functionalized antitumor antibiotic and is useful for the preparation of analogs of the putative pharmacophore of the Ras farnesyltransferase inhibitor manumycin
A new NF-κB inhibitor based on the amino-epoxyquinol core of DHMEQ
Saitoh, Tsuyoshi,Shimada, Chika,Takeiri, Masatoshi,Shiino, Mitsuhiro,Ohba, Shigeru,Obata, Rika,Ishikawa, Yuichi,Umezawa, Kazuo,Nishiyama, Shigeru
, p. 5638 - 5642 (2010)
The amino-epoxyquinols 6a and 6b were synthesized as soluble derivatives of an NF-κB inhibitor DHMEQ (1). In spite of the opposite configuration from 1, 6b rather than 6a affected the deactivation of NF-κB, based on NO secretion and MALDI-TOF MS analysis.
Synthesis and evaluation of a cyclopropane derivative of DHMEQ
Yasui, Eiko,Takayama, Kan,Nakago, Takahiro,Takeda, Nobuyuki,Imamura, Yasutada,Nagumo, Shinji
, p. 304 - 307 (2014/04/17)
Dehydroxymethylepoxyquinomycin (DHMEQ, 1) is well known to inhibit nuclear factor-kappa B (NF-κB), which is closely associated with immune, inflammatory, and apoptotic processes as an inducible transcription factor. The inhibitory effect seems to be the r
Synthesis of (-)-LL-C10037α and related manumycin-type epoxyquinols
Wipf,Kim,Jahn
, p. 1549 - 1561 (2007/10/02)
Starting with N-allyloxycarbonyl-protected 2,5-dimethoxyaniline, hypervalent iodine oxidation protocols and selective enone epoxidation provides the Streptomyces metabolite LL-C10037α in nine steps and 7-10% overall yield. In an asymmetric variant of this strategy, (R,R)-pentane-2,4-diol is used as a chiral acetalization agent. The resulting semiquinone spiroacetal, due to an ortho-acylamino substituent that restricts the 1,3-dioxane ring conformation, undergoes face-selective epoxidation and is further functionalized to give (-)-LL-C10037α in 94% ee. These pathways represent the first syntheses of the highly functionalized mC7N core of the manumycins and have been further extended toward the preparation of analogs for SAR studies of this class of antitumor antibiotics. Manumycins inhibit the farnesylation of Ras-protein by PFTase (protein farnesyltransferase).
