867-13-0Relevant articles and documents
Pyridyl-Amides as a Multimode Self-Assembly Driver for the Design of a Stimuli-Responsive π-Gelator
Kartha, Kalathil K.,Praveen, Vakayil K.,Babu, Sukumaran Santhosh,Cherumukkil, Sandeep,Ajayaghosh, Ayyappanpillai
, p. 2250 - 2256 (2015)
An oligo(p-phenylenevinylene) (OPV) derivative connected to pyridyl end groups through an amide linkage (OPV-Py) resulted in a multistimuli-responsive π-gelator. When compared to the corresponding OPV π-gelator terminated by a phenyl-amide (OPV-Ph), the aggregation properties of OPV-Py were found to be significantly different, leading to multistimuli gelation and other morphological properties. The pyridyl moiety in OPV-Py initially interferes with the amide H-bonded assembly and gelation, however, protonation of the pyridyl moiety with trifluoroacetic acid (TFA) facilitated the formation of amide H-bonded assembly leading to gelation, which is reversible by the addition of N,N-diisopropyethylamine (DiPEA). Interestingly, addition of Ag+ ions to a solution of OPV-Py facilitated the formation of a metallo-supramolecular assembly leading to gelation. Surprisingly, ultrasound-induced gelation was observed when OPV-Py was mixed with a dicarboxylic acid (A1). A detailed study using different spectroscopic and microscopic experimental techniques revealed the difference in the mode of assembly in the two molecules and the multistimuli-responsive nature of the OPV-Py gelation.
One-pot synthesis and antimicrobial of novel 6-ethoxy-6-oxido-3-oxo(thioxo) (imino)-5-substituted-2,7-dihydro-1,2,4-triazolo[3,4-e][1,2,3]diazaphospholes
Ali, Tarik E.,Assiri, Mohammed A.
, p. 965 - 969 (2021)
A series of novel 6-ethoxy-6-oxido-3-oxo(thioxo)(imino)-5-substituted-2,7-dihydro-1,2,4-triazolo[3,4-e][1,2,3]diazaphospholes 2a-f was synthesized and characterized by IR and NMR (1H, 13C, and 31P) spectroscopic analysis. The methodology developed was one-pot three-component reaction of ethyl bromoacetate, triethyl phosphite and carbo(thio)(amino)hydrazides. The synthesized compounds were screened for their antimicrobial activities. 6-Ethoxy-6-oxido-3-oxo(thioxo)-5-phenyl-2,5,7-trihydro-1,2,4-triazolo[3,4-e][1,2,3]diazaphospholes (2c,d) exhibited significantly higher antimicrobial effects against the tested bacterial and fungal strains compared to other compounds and standard drug.
Regioselective Synthesis of Novel Functionalized Pyrano[2′,3′:4,5]pyrimido[1,6-b][1,2,4,5]triazaphosphepines
Ali,Assiri,Yahia,Zahran,Meselhy,Hussien
, p. 79 - 84 (2021/03/04)
Abstract: The reactions of6-acetyl-3-amino-4-imino-7-methyl-5-phenyl-3,5-dihydro-4H-pyrano[2,3-d]pyrimidine with triethyl phosphite and some electrophilicreagents, namely 1,2-dibromoethane, oxalyl chloride, chloroacetyl chloride, andethyl chloroacetate, were studied. These one-pot three-component reactionsregioselectively afforded four new11-acetyl-2-ethoxy-10-methyl-12-phenylpyrano[2′,3′:4,5]pyrimido[1,6-b][1,2,4,5λ5]triazaphosphepin-2-ones in69–73% yields.
Enantioselective Michael addition to vinyl phosphonatesviahydrogen bond-enhanced halogen bond catalysis
Erkman, Kristin,J?rving, Ivar,Kaasik, Mikk,Kanger, T?nis,Mart?nova, Jevgenija,Metsala, Andrus
, p. 7561 - 7568 (2021/06/09)
An asymmetric Michael addition of malononitrile to vinyl phosphonates was accomplished by hydrogen bond-enhanced bifunctional halogen bond (XB) catalysis. NMR titration experiments were used to demonstrate that halogen bonding, with the support of hydrogen-bonding, played a key role in the activation of the Michael acceptors through the phosphonate group. This is the first example of the use of XBs for the activation of organophosphorus compounds in synthesis. In addition, the iodo-perfluorophenyl group proved to be a better directing unit than different iodo- and nitro-substituted phenyl groups. The developed approach afforded products with up to excellent yields and diastereoselectivities and up to good enantioselectivities.
BRYOSTATIN COMPOUNDS FOR ENHANCEMENT OF IMMUNOTHERAPY
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Page/Page column 95-96, (2020/12/07)
Provided herein is the use of bryostatin agents to selectively enhance expression, translocation and/or cell surface presentation of an antigen in target cells of interest to modulate immunogenicity of the target cells. Aspects of the methods include, administering an effective amount of a bryostatin agent to a subject to modulate immunogenicity of target cells. The subject methods include a method of treating cancer, including administering to a subject an effective amount of a bryostatin agent to enhance cell surface antigen or neoantigen presentation on target cells of the subject, and administering to the subject a therapeutically effective amount of a therapeutic agent that specifically binds the cell surface antigen to treat the subject for cancer. Aspects of the subject methods also include use of the bryostatin agents to sensitize the target cells to clearance by the subject's immune system.
Alkyl phosphonate preparing method
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Paragraph 0040; 0041; 0042; 0043; 0044-0067; 0096; 0097, (2017/10/07)
The invention provides an alkyl phosphonate preparing method. The method comprises: performing an Arbuzov reaction on compound A and compound B in a continuous reaction apparatus, and continuously discharging the product obtained from the reaction from the continuous reaction apparatus during the reaction procedure, to obtain alkyl phosphonate. The reaction temperature in the reaction procedure is T1; either of compound A and compound B having a lower boiling point has a boiling point at a standard atmosphere pressure to be T2; T1 is higher than T2 by 10-40 DEG C; and the reaction pressure in the reaction procedure is 0.5-2.0 MPa. The preparing method in the invention may use halohydrocarbon having large steric hindrance and lower polarizability of carbon-halogen bond as compound A, thereby effectively expanding a selection range of substrate, and correspondingly expanding the types of alkyl phosphonate prepared by using the Arbuzov reaction.
Synthesis method of triethyl phosphonoacetate
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Paragraph 0017; 0019; 0021; 0024; 0026; 0029; 0031, (2017/08/27)
Relating to the field of organic compound synthesis, the invention provides a synthesis method of triethyl phosphonoacetate. Triethyl phosphate and ethyl chloroacetate are taken as the raw materials to carry out Michael arbuzov rearrangement reaction, thus obtaining triethyl phosphonoacetate. The chemical reaction formulas of the synthesis method are: CH2ClCOOH+C2H5OH to C4H7ClO2+H2O, C4H7ClO2+C6H15O3P to C8H17O5P+C2H5Cl. The method provided by the invention solves the problems of high energy consumption, high cost and low product purity in the traditional process, also solves the problem of byproduct application in a synthetic environment, and achieves good economic and social benefits.
Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives
Maeda, Hajime,Wada, Hidenori,Mukae, Hirofumi,Mizuno, Kazuhiko
, p. 29 - 41 (2016/11/16)
Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4?+?2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.
Design, synthesis and SAR study of novel sulfonylureas containing an alkenyl moiety
Wei, Wei,Cheng, Dandan,Liu, Jingbo,Li, Yuxin,Ma, Yi,Li, Yonghong,Yu, Shujing,Zhang, Xiao,Li, Zhengming
, p. 8356 - 8366 (2016/09/09)
A series of sulfonylurea compounds was designed and synthesized via introducing an alkenyl moiety into the aryl-5 position and most title compounds exhibited enhanced antifungal activities and limited herbicidal activities compared with chlorsulfuron. Then, a CoMSIA calculation for antifungal activities was carried out to establish a 3D-QSAR model in which a cross-validated q2 of 0.585 and a correlation coefficient r2 of 0.989 were obtained. The derived model revealed that hydrophobic and electrostatic fields were the two most important factors for antifungal activity. Structure optimization was performed according to the CoMSIA model and compound 9z was found to be as potent as chlorothalonil in vitro against C. cornigerum, the pathogen of the wheat sharp eyespot disease. In order to study the fungicidal mechanism, 9z was successfully docked into yeast AHAS using a flexible molecular docking method and the resulting binding pattern was similar to that of chlorimuron-ethyl, indicating that the antifungal activity of compounds 9 was probably due to the inhibition of fungal AHAS.
Long-Range Reactivity Modulations in Geranyl Chloride Derivatives
Reardon, Michael B.,Xu, Muyun,Tan, Qingzhe,Baumgartel, P. George,Augur, Danielle J.,Huo, Shuanghong,Jakobsche, Charles E.
, p. 10964 - 10974 (2016/11/29)
Derivatives of geraniol are versatile synthetic intermediates that are useful for synthesizing a variety of terpenoid natural products; however, the results presented herein show that subtle differences in the structures of functionalized geranyl chlorides can significantly impact their abilities to function as effective electrophiles in synthetic reactions. A series of focused kinetics experiments identify specific structure-activity relationships that illustrate the importance not only of steric bulk, but also of electronic effects from distant regions of the molecules that contribute to their overall levels of reactivity. Computational modeling suggests that destabilization of the reactant by filled-filled orbital mixing events in some, but not all, conformations may be a critical contributor to these important electronic effects.
