91026-00-5Relevant articles and documents
Electrochemical synthesis method of 3,4-dibromomalayimide
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Paragraph 0120-0121, (2022/01/10)
The present invention relates to the field of organic synthesis technology, in particular to a 3,4-dibromo maleimide electrochemical synthesis method, maleimide as the starting material, to inexpensive, safe and readily available bromide as a bromine sour
Scalable preparation of stable and reusable silica supported palladium nanoparticles as catalysts for N-alkylation of amines with alcohols
Alshammari, Ahmad S.,Natte, Kishore,Kalevaru, Narayana V.,Bagabas, Abdulaziz,Jagadeesh, Rajenahally V.
, p. 141 - 149 (2020/01/06)
The development of nanoparticles-based heterogeneous catalysts continues to be of scientific and industrial interest for the advancement of sustainable chemical processes. Notably, up-scaling the production of catalysts to sustain unique structural features, activities and selectivities is highly important and remains challenging. Herein, we report the expedient synthesis of Pd-nanoparticles as amination catalysts by the reduction of simple palladium salt on commercial silica using molecular hydrogen. The resulting Pd-nanoparticles constitute stable and reusable catalysts for the synthesis of various N-alkyl amines using borrowing hydrogen technology without the use of any base or additive. By applying this Pd-based catalyst, functionalized and structurally diverse N-alkylated amines as well as some selected drug molecules were synthesized in good to excellent yields. Practical and synthetic utility of this Pd-based amination protocol has been demonstrated by upscaling catalyst preparation and amination reactions to several grams-scales as well as recycling of catalyst. Noteworthy, this Pd-catalyst preparation has been up-scaled to kilogram scale and catalysts prepared in both small (1 g) and large-scale (kg) exhibited similar structural features and activity.
Discovery of new effective N-alkyl-3,4-diarylmaleimides-based drugs for reversing the bacterial resistance to rhodamine 6G in Bacillus subtilis
Mendoza-Macías, Claudia Leticia,Solorio-Alvarado, Cesar Rogelio,Alonso-Castro, Angel Josabad,Alba-Betancourt, Clara,Deveze-álvarez, Martha Alicia,Padilla-Vaca, Felipe,Reyes-Gualito, Arturo
, p. 1429 - 1438 (2019/11/28)
Multidrug resistance (MDR) is a great concern worldwide. There is a great need to develop new drugs with the potential to attack target cells that show MDR phenotype. The purpose of this study was to assess the reversing effect of new N-alkyl-3,4-diarylma
A mild and selective protecting and reversed modification of thiols
Li, Xiangmin,Li, Hongxian,Yang, Wei,Zhuang, Jinchen,Li, Hao,Wang, Wei
supporting information, p. 2660 - 2663 (2016/06/01)
One selective thiol-protecting study has been investigated for a wide range of thiols including general thiols and thiols containing multiple functional groups. The reactions of bromomaleimides and thiols under the mild condition afforded the protected products in excellent yields. The thiols can be recovered very quickly using dithiothreitol (DTT) under the mild condition.
Maleimide-based acyclic enediyne for efficient DNA-cleavage and tumor cell suppression
Song, Depeng,Sun, Shiyuan,Tian, Yu,Huang, Shuai,Ding, Yun,Yuan, Yuan,Hu, Aiguo
supporting information, p. 3195 - 3200 (2015/04/27)
A pH-sensitive acyclic enediyne (1) was synthesized for efficient DNA-cleavage and tumor cell suppression. Unlike other acyclic enediynes, this novel enediyne transforms into a highly reactive enediyne (2) in an acidic environment only, which undergoes Be
A mild synthesis of N-functionalised bromomaleimides, thiomaleimides and bromopyridazinediones
Casta?eda, Lourdes,Wright, Zo? V.F.,Marculescu, Cristina,Tran, Trang M.,Chudasama, Vijay,Maruani, Antoine,Hull, Elizabeth A.,Nunes, Jo?o P.M.,Fitzmaurice, Richard J.,Smith, Mark E.B.,Jones, Lyn H.,Caddick, Stephen,Baker, James R.
supporting information, p. 3493 - 3495 (2013/07/05)
Bromomaleimides are useful building blocks in synthesis and powerful reagents for the selective chemical modification of proteins. A mild new synthesis of these reagents is described, along with the convenient transferability of the approach to dithiomale
Development of antiproliferative phenylmaleimides that activate the unfolded protein response
Muus, Ulrike,Hose, Curtis,Yao, Wei,Kosakowska-Cholody, Teresa,Farnsworth, David,Dyba, Marzena,Lountos, George T.,Waugh, David S.,Monks, Anne,Burke Jr., Terrence R.,Michejda, Christopher J.
supporting information; experimental part, p. 4535 - 4541 (2010/08/22)
The current paper presents the synthesis and evaluation of a series of maleimides that were designed to inhibit the Cdc25 phosphatase by alkylation of catalytically essential cysteine residues. Although in HepB3 cell culture assays the analogues did exhib
Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction
Cheng, Chia-Fu,Lai, Zhen-Chang,Lee, Yean-Jang
, p. 4347 - 4353 (2008/09/20)
Maleic anhydride 1 of Antrodia camphorate, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only five steps, in 40% overall yield from commercially available succinic anhydride. The crucial antrodimid
Synthesis of substituted bis(heteroaryl)maleimides
Dubernet, Mathieu,Caubert, Virginie,Guillard, Jér?me,Viaud-Massuard, Marie-Claude
, p. 4585 - 4593 (2007/10/03)
Substituted bis(fur-2-yl), bis(fur-3-yl) and bis(thien-2-yl) maleimides with potential antidiabetic properties are described. Their synthesis involves, as a key step, a Suzuki cross-coupling between various boron derivatives and the diiodomaleimides. Therefore, a wide range of substituted symmetric and non-symmetric maleimide derivatives can be prepared.
Revised Structures of N-Substituted Dibrominated Pyrrole Derivatives and Their Polymeric Products. Termaleimide Models with Low Optical Band Gaps
Choi, Dong-Sook,Huang, Shenlin,Huang, Mingsheng,Barnard, Thomas S.,Adams, Richard D.,Seminario, Jorge M.,Tour, James M.
, p. 2646 - 2655 (2007/10/03)
This paper describes an unexpected rearrangement/oxidation of N-substituted 2,5-dibromopyrroles upon treatment with HNO3. The bromides migrate from the 2,5-positions to the 3,4-positions with subsequent oxidation at the 2,5-positions to afford N-substituted 3,4-dibromomaleimides; the structure was confirmed by single-crystal X-ray analysis. The maleimides were then polymerized to the poly(N-substituted-3,4-maleimide)s with copper bronze. This constitutes a revision of structure for the monomers and polymers. The propensity for the dibromide migration was further confirmed by treatment of N-benzyl-2,5-dibromopyrrole under nonoxidative acidic conditions (p-TsOH) to afford N-benzyl-3,4-dibromopyrrole; both the starting material and product structures were confirmed by single-crystal X-ray analysis. Several termaleimides were prepared from pyrrole, maleic anhydride, and citraconic anhydride. These trimeric compounds underwent enormous shifts in their optical absorbance maxima (ca. 200 nm) when bases or nucleophilic solvents were added. Therefore, the termaleimides served as excellent models for the polymeric systems that had undergone shifts of 350-400 nm upon treatment with the same additives. Ab initio Hartree-Fock and density functional theory were utilized to assess the minimum conformation of the trimeric system. Both terminal maleimides appear canted 37° relative to the central maleimide unit. As the two end maleimide units were computationally forced into closer proximity, there was a dipolar stabilization that ensued between the two terminal maleimides with the formation of a 1,3-dioxetane. However, it is unlikely that there could be the formation of an isolable 1,3-dioxetane due to the large energy difference between the canted structure and the dioxetane. A significant decrease in the HOMO-LUMO energy of 13 kcal/mol was calculated upon formation of the 1,3-dioxetane, suggesting that nucleophiles likely move the canted structure more toward a planar form via addition to the α,β-unsaturated carbonyl units.
