5410-10-6Relevant academic research and scientific papers
N-Acetyliminodiacetate dimethyl ester
Prayzner, Paula,Ojadi, Emmanuel C. A.,Golen, James A.,Williard, Paul G.
, p. 112 - 113 (1996)
N-Acetyliminodiacetate dimethyl ester, C8H13NO5, was prepared for the synthesis of 3,4-diphenylpyrrole in a multi-step synthetic route to a model porphyrin. The technique used in this preparation yielded colorless crystals of high purity. Site geometry around the central N atom is nearly trigonal planar.
Total synthesis and biological evaluation of 7-hydroxyneolamellarin A as hypoxia-inducible factor-1α inhibitor for cancer therapy
Li, Guangzhe,Shao, Yujie,Pan, Yue,Li, Yueqing,Wang, Yang,Wang, Liu,Wang, Xu,Shao, Kun,Wang, Shisheng,Liu, Naixuan,Zhang, Jingdong,Zhao, Weijie,Nakamura, Hiroyuki
supporting information, (2021/09/04)
7-Hydroxyneolamellarin A (7-OH-Neo A, 1), a natural marine product derived from sponge Dendrilla nigra, was first synthesized with 10% overall yield under the instruction of convergent synthetic strategy. We found that 7-OH-Neo A could attenuate the accum
Structure-activity relationships study of neolamellarin A and its analogues as hypoxia inducible factor-1 (HIF-1) inhibitors
Li, Guangzhe,Dong, Huijuan,Ma, Yao,Shao, Kun,Li, Yueqing,Wu, Xiaodan,Wang, Shisheng,Shao,Zhao, Weijie
supporting information, p. 2327 - 2331 (2019/07/09)
The novel marine pyrrole alkaloid neolamellarin A derived from sponge has been shown to inhibit hypoxia-induced HIF-1 activity. In this work, we designed and synthesized neolamellarin A and its series of derivatives by a convergent synthetic strategy. The HIF-1 inhibitory activity and cytotoxicity of these compounds were evaluated in Hela cells by dual-luciferase reporter gene assay and MTT assay, respectively. The results showed that neolamellarin A 1 (IC50 = 10.8 ± 1.0 μM) and derivative 2b (IC50 = 11.9 ± 3.6 μM) had the best HIF-1 inhibitory activity and low cytotoxicity. Our SAR research focused on the effects of key regions aliphatic carbon chain length, aromatic ring substituents and C-7 substituent on biological activity, providing a basis for the subsequent research on the development of novel pyrrole alkaloids as HIF-1 inhibitors and design of small molecule probes for target protein identification.
Total synthesis and application of natural product of 7-hydroxy novel lamellarin A and analogues of natural product of 7-hydroxy novel lamellarin A
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Paragraph 0063-0065, (2019/11/12)
The invention belongs to the technical field of pharmaceutical and chemical engineering, and provides total synthesis and application of a natural product of 7-hydroxy novel lamellarin A and analoguesof the natural product of the 7-hydroxy novel lamellarin A. The invention provides the 7-hydroxy novel lamellarin A natural product and the series of analogues of the 7-hydroxy novel lamellarin A natural product. Tested compounds all have medium to good HIF-1 inhibitory activity, and have no market toxicity under the effective inhibition concentration of HIF-1 of the tested compounds, and it is indicated that the compounds have the potential for treating cancers by inhibiting transcription activating of the HIF-1.
Synthesis of 1',2',3',4',5'-pentamethyl-3,4-diphenylazaferrocene and its enantioselective C-2 functionalization via (-)-sparteine-mediated lithiation
Fukuda, Tsutomu,Koga, Yasuyuki,Iwao, Masatomo
experimental part, p. 1237 - 1248 (2009/06/28)
Lithiation of 1',2',3',4',5'-pentamethyl-3,4-diphenylazaferrocene (9) with sec-BuLi/(-)-sparteine (2) in Et2O at -78 °C followed by quenching with electrophiles gave the C-2 functionalized azaferrocenes (17) in good enantioselectivities (up to
Nonplanar distortion modes for highly substituted porphyrins
Medforth, Craig J.,Senge, Mathias O.,Smith, Kevin M.,Sparks, Laurie D.,Shelnutt, John A.
, p. 9859 - 9869 (2007/10/02)
The syntheses, structures, and spectroscopic properties of some novel dodecaphenyl- and dodecaalkylporphyrins have been investigated with the aim of designing model compounds to aid in evaluating theoretical models of porphyrin nonplanarity. It was found that dodecaphenylporphyrin (3) and the dodecaalkylporphyrins 4a-c could be prepared using standard synthetic procedures and that these porphyrins adopted very distorted nonplanar structures in the crystalline state. In the crystal structure of 3 the pyrrole rings were tilted with respect to the mean plane of the porphyrin to give a saddle conformation, whereas in the crystal structure of the nickel(II) complex of 4c (Ni4c) the pyrrole rings were twisted with respect to the mean plane to give a ruffled conformation. Nonplanar conformations with the same distortion modes were obtained as minimum energy structures for Ni3 and Ni4c using a molecular mechanics force field, which showed that the observed nonplanar conformations were due to steric repulsions between the peripheral substituents. Low-temperature NMR spectra indicated that the solution conformations of 3 and Ni4c were consistent with those found in the crystal structures. Several conformations of Ni4b and Ni4c with different quasi-axial and quasi-equatorial orientations of the alkyl chains were observed in solution, and saddle and ruffled distortion modes were clearly differentiated for the dications and nickel(II) complexes of porphyrins 4b and 4c. Finally, an attempt was made to synthesize the dodecaalkylporphyrin 5 using the same conditions applied to porphyrins 4a-c. This gave only the 5,15-dihydroporphyrin 6, presumably because the more spatially demanding six-membered ring prevented the oxidation of 6 to porphyrin 5 using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
