- Nitroketene dithioacetal chemistry. Part 2: Synthesis of novel 4-(alkylsulfanyl)-2-[1-nitromethylidene]-1,3-dithioles from the dipotassium salt of 2-nitro-1,1-ethylenedithiol
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The reaction of the dipotassium salt of 2-nitro-1,1-ethylenedithiol with long chain alkyl halides in acetonitrile medium furnished the novel heterocyclic, 4-(alkylsulfanyl)-2-[1-nitromethylidene]-1,3-dithioles.
- Rao, H. Surya Prakash,Sakthikumar,Vanitha,Kumar, S. Siva
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- Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
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Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.
- Galkin, Konstantin I.,Krivodaeva, Elena A.,Romashov, Leonid V.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Burykina, Julia V.,Ananikov, Valentine P.
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supporting information
p. 8338 - 8342
(2016/07/19)
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- Design, synthesis and biological evaluation of novel inosine 5′-monophosphate dehydrogenase (IMPDH) inhibitors
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This study is based on our attempts to further explore the structure-activity relationship (SAR) of VX-148 (3) in an attempt to identify inosine 5′-mono-phosphate dehydrogenase (IMPDH) inhibitors superior to mycophenolic acid. A five-point pharmacophore developed using structurally diverse, known IMPDH inhibitors guided further design of novel analogs of 3. Several conventional as well as novel medicinal chemistry strategies were tried. The combined structure- and ligand-based approaches culminated in a few analogs with either retained or slightly higher potency. The compounds which retained the potency were also checked for their ability to inhibit human peripheral blood mononuclear cells proliferation. This study illuminates the stringent structural requirements and strict SAR for IMPDH II inhibition.
- Dunkern, Torsten,Chavan, Sunil,Bankar, Digambar,Patil, Anuja,Kulkarni, Pritee,Kharkar, Prashant S.,Prabhu, Arati,Goebel, Heike,Rolser, Edith,Burckhard-Boer, Waltraud,Arumugam, Premkumar,Makhija, Mahindra T.
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p. 408 - 419
(2014/06/09)
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- HETEROCYCLIC SULFONAMIDE DERIVATIVES USEFUL AS MEK INHIBITORS
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The present invention relates to compounds of Formula (IA) Where R1a, R1b, X, R2a, R2b, W, R3, R4, and R5 are as defined herein as well as pharmaceutically acceptable salts thereof. The compounds have been shown to act as MEK inhibitors which may be useful in the treatment of hyperproliferative diseases, like cancer and inflammation.
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Page/Page column 45
(2011/06/11)
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- Heterocyclic Sulfonamide Derivatives
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The present invention relates to compounds of Formula I where R1a, R1b, X, R2a, R2b, W, R3, R4, and R5 are as defined herein as well as pharmaceutically acceptable salts thereof. The compounds have been shown to act as MEK inhibitors which may be useful in the treatment of hyperproliferative diseases, like cancer and inflammation.
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Page/Page column 16
(2011/08/08)
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- PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH INSECTICIDAL ACTIVITIES
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The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhopper, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus, carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.
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(2009/05/28)
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- PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH BIOCIDAL ACTIVITIES
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The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhoppei, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus, carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.
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(2009/01/20)
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- NITROMETHYLENE DERIVATIVES AND THEIR USE
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The present invention discloses nitromethylene derivatives and the uses thereof. These derivatives are obtained by adding ring structure onto the known nitromethylene compounds, by which both their stability for light and their liposolubility are increased. Furthermore, by using the substituents linked to ether bond, the steric orientation of the nitro group and the liposolubility of the compounds are controlled. The insecticidal activity tests show that the compounds and their derivatives of the invention display high efficiency on killing various destructive insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhopper, plant hpooer, thrips and white fly.
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(2008/06/13)
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- Synthesis and bioactivities of novel neonicotinoids dioxolane compounds
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As candidates for the screening of neonicotinoid insecticides, nine novel compounds were designed and synthesised via Mannich reaction of (1,3-dioxolane-4-yl)methyl-2-(nitromethylene) imidazoline with corresponding primary amines and formaldehyde. Preliminary bioassays indicated that most of these compounds had moderate insecticidal activities against pea aphids.
- Tian, Zhongzhen,Li, Zhong,Huang, Qingchun,Xu, Xiaoyong,Yu, Tao,Wu, Yingli,Qian, Xuhong
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p. 626 - 628
(2007/10/03)
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- Nitroketene acetal chemistry. 3. Facile synthesis of nitroacetic acid triarylmethyl ortho esters from 1,1-Di(methylsulfanyl)-2-nitroethylene
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The reaction of 1,-di(methylsulfanyl)-2-nitroethylene, benzyl alcohols, and sodium hydride furnishes crystalline triarylmethyl ortho esters of nitroacetic acid.
- Rao, H. Surya Prakash,Sivakumar
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p. 4524 - 4527
(2007/10/03)
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- Aminopyridazines as acetylcholinesterase inhibitors
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Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 μM on homogenized rat striatum AChE), a series of 3-amino-6- phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high AChE inhibition are as follows: (i) presence of a central pyridazine ring, (ii) necessity of a lipophilic cationic head, (iii) change from a 2- to a 4-5-carbon units distance between the pyridazine ring and the cationic head. Among all the derivatives investigated, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6- phenylpyridazine (3y), which shows an IC50 of 0.12 μM on purified AChE (electric eel), was found to be one of the most potent anti-AChE inhibitors, representing a 5000-fold increase in potency compared to minaprine.
- Contreras, Jean-Marie,Rival, Yveline M.,Chayer, Said,Bourguignon, Jean-Jacques,Wermuth, Camille G.
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p. 730 - 741
(2007/10/03)
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- A diketene imine derivative and process for preparing same
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The invention relates to the novel compound of formula (I), chemically 1-{2-[(5-N,N-dimethylaminomethyl-2-furyl)-methylthio]ethyl}-2-{2-[(5-N,N-dimethylaminomethyl-2-furyl)-methylthio]-1-ethylamino}-3-nitro-4-nitromethylene-2-azetine, which is a useful key intermediate in the synthesis of 1-{2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethyl}-amino-1-methylamino-2-nitroethylene (generic name: ranitidine), a known H-2 receptor antagonist. The invention further relates to a process for the preparation of the compound of formula (I), which can be carried out in one simple process step on industrial scale, too. The compound of formula (I) can easily be transformed to ranitidine in one simple step.
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- INTERMEDIATES FOR UREA AND THIOUREA DERIVATIVES
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This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compounds, a process for the preparation thereof and an anti-ulcer agent containing the same.
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