cas 870-46-2, tert-Butyl carbazate | Articles data

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A novel poly(l -glutamic acid) dendrimer based drug delivery system with both pH-sensitive and targeting functions
The functionalization of pH-sensitiveness and cellular targeting is a promising strategy to fabricate drug delivery systems with high efficiency, high selectivity and low toxicity. In this paper, a poly(l-glutamic acid) dendrimer based drug delivery system with both pH-sensitive and targeting functions is reported. Poly(l-glutamic acid) dendrimers with a polyhedral oligomeric silsesquioxane (POSS) nanocubic core were synthesized. Its globular morphology and compact structure with multiple peripheral functional groups made it suitable for drug delivery. The OAS-G3-Glu dendrimer was conjugated with doxorubicin via pH-sensitive hydrazine bonds and targeting moiety (biotin). The cellular internalization and antitumor effects of the conjugates was evaluated in vitro. Both DLS and TEM results indicated that the conjugates aggregated into nanoparticles with diameters around 50 nm. The release rates of doxorubicin at pH 5.0 were much faster than those at pH 7.0 due to the acid cleavage of the hydrazine bonds. The internalization study revealed that the cellular uptake of the biotin modified conjugates was mainly through receptor-mediated endocytosis. These results indicate that our poly(l-glutamic acid) dendrimers with OAS core are promising vectors for fabricating smart and targeting drug delivery systems.
Yuan, Hui,Luo, Kui,Lai, Yusi,Pu, Yuji,He, Bin,Wang, Gang,Wu, Yao,Gu, Zhongwei
p. 953 - 962
(2010)
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Preparation method of high-purity tert-butyl carbazole
The invention relates to the technical field of drug synthesis, in particular to a preparation method of high-purity tert-butyl carbazole. After the completion of the reaction, the hydrazine monohydrate is neutralized with a base, extracted with a solvent, concentrated, and then crystallized by a weak polar solvent to give a tert-butyl carbazole product. The preparation method of the tert-butyl carbazole can obtain the high-purity product (≥ 99.5%), has high yield (≥ 90%), is simple to operate, and is suitable for industrial large-scale production.
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Paragraph 0029-0036

(2021/09/21)

Sitagliptin impurity and preparation method and detection method thereof
The novel impurity can provide standard reference for quality control of sitagliptin and safety detection of clinical medication, so that safety and reliability of clinical medication are guaranteed. In addition, the preparation method of the impurity compound provided by the invention is simple to operate and mild in reaction conditions, can obtain impurity compounds with high purity and high yield, is used for further researching impurity properties, and provides technical support for the content control of sitagliptin compounds and the safety problems of sitagliptin. The sitagliptin impurity detection method can perform targeted qualitative detection on the impurities, is high in detection precision, and is beneficial to the technical means for detecting impurities in the sitagliptin, so that the quality of the sitagliptin impurity is controlled.
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Paragraph 0046; 0047

(2021/10/05)

Elastic targeting polypeptide-based medicine-carrying nanoparticle as well as preparation method and application thereof
The invention discloses an elastic targeting polypeptide-based medicine-carrying nanoparticle. The nanoparticle is prepared from an elastic targeting polypeptide and a modified medicine, wherein the modified medicine is a modified paclitaxel PTX-LEV-MECH or modified salinomycin Sail-ABA-MPBH. The elastic targeting polypeptide-based medicine-carrying nanoparticle provided by the invention is 100nmor below in particle size, so that the dispersion degree is low, the medicine carrying rate is high, and the nanoparticle can be combined with in-vivo albumin for transferring and carrying medicine, and also can be combined with acidic rich cysteine specifically secreted by tumor cells, the drug is concentrated in the acidic environment, the breast cancer in-situ cancer is targeted for killing, and the toxic and side effects of the drug on the whole body are reduced; and the efficacy of treating breast cancer is increased and improved by utilizing the synergistic effect of two nanoparticles, the occurrence of the metastasis of the breast cancer cells through a lymphatic system and a blood system is reduced, and the occurrence of serious complications such as medical-source lymphatic edemacaused by a lymph node sweeping surgery is reduced.
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Paragraph 0029-0031; 0039-0041

(2020/07/15)

Synthesis method of single BOC protection double-amino compound
The invention relates to the field of fine chemical engineering, in particular to a synthesis method of a single BOC protection double-amino compound. The synthesis method comprises the steps that firstly, an acid compound and double-amino are subjected to complex reaction, then moderate BOX acid anhydride is added for reaction, and a product is obtained. The method is simple in reaction step, high in product yield and purity and suitable for industrial production.
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Paragraph 0022; 0023

(2018/06/21)

Multiprotein Dynamic Combinatorial Chemistry: A Strategy for the Simultaneous Discovery of Subfamily-Selective Inhibitors for Nucleic Acid Demethylases FTO and ALKBH3
Dynamic combinatorial chemistry (DCC) is a powerful supramolecular approach for discovering ligands for biomolecules. To date, most, if not all, biologically templated DCC systems employ only a single biomolecule to direct the self-assembly process. To expand the scope of DCC, herein, a novel multiprotein DCC strategy has been developed that combines the discriminatory power of a zwitterionic “thermal tag” with the sensitivity of differential scanning fluorimetry. This strategy is highly sensitive and could differentiate the binding of ligands to structurally similar subfamily members. Through this strategy, it was possible to simultaneously identify subfamily-selective probes against two clinically important epigenetic enzymes: FTO (7; IC50=2.6 μm) and ALKBH3 (8; IC50=3.7 μm). To date, this is the first report of a subfamily-selective ALKBH3 inhibitor. The developed strategy could, in principle, be adapted to a broad range of proteins; thus it is of broad scientific interest.
Das, Mohua,Yang, Tianming,Dong, Jinghua,Prasetya, Fransisca,Xie, Yiming,Wong, Kendra H. Q.,Cheong, Adeline,Woon, Esther C. Y.
supporting information
p. 2854 - 2867
(2018/09/25)

Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists
The transient receptor potential vanilloid type-2 (TRPV2) protein is a nonselective Ca2+ permeable channel member of the TRPV subfamily, still considered an orphan TRP channel due to the scarcity of available selective and potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure-activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain fatty acid ethanolamides or primary amides acting as TRPV2 antagonists. Both synthetic and endogenous antagonists exhibited differential inhibition against known TRPV2 agonists characterized by distinct kinetic profiles. These findings represent the first example of both synthetic and naturally occurring TRPV2 modulators with efficacy in the submicromolar/low-micromolar range, which will be useful for clarifying the physiopathological roles of this receptor, its regulation, and its targeting in pathological conditions.
Schiano Moriello, Aniello,López Chinarro, Silvia,Novo Fernández, Olalla,Eras, Jordi,Amodeo, Pietro,Canela-Garayoa, Ramon,Vitale, Rosa Maria,Di Marzo, Vincenzo,De Petrocellis, Luciano
p. 8255 - 8281
(2018/09/25)

Visible-light induced copper(i)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes
Visible light mediated copper catalysed denitrogenative oxidative coupling of 2-hydrazinopyridines with terminal alkynes to form 2-(alkyl/arylethynyl) pyridines in the presence of O2 at room temperature is reported with 42 examples. This is the first report on visible light stimulated N2 elimination by an in situ generated copper(ii) superoxo/peroxo complex. N2 and water are the only by-products. The green chemistry metrics evaluation signifies that the current method is ecofriendly and economically feasible. This method allows the green synthesis of mGluR5 receptor antagonists, 2-methyl-6-(phenylethynyl)pyridine (MPEP) and 2-((3-methoxyphenyl)ethynyl)-6-methylpyridine (M-MPEP).
Charpe, Vaibhav Pramod,Hande, Aniket A.,Sagadevan, Arunachalam,Hwang, Kuo Chu
supporting information
p. 4859 - 4864
(2018/11/21)

The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketimines
An asymmetric organocatalytic addition of fluorinated phenylsulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine. This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7:1 dr) and excellent enantioselectivity (up to 98/96% ee).
Urban,Franc,Hofmanová,Císa?ová,Vesely
supporting information
p. 9071 - 9076
(2017/11/14)

A reusable and naked-eye molecular probe with aggregation-induced emission (AIE) characteristics for hydrazine detection
We report a fluorogenic probe for naked-eye sensing of hydrazine in solution and in the gaseous phase. The probe based on tetraphenylethylene (TPE) with aggregation-induced emission (AIE) characteristics shows OFF-ON fluorescence as observed by thin-layer chromatography (TLC) upon treatment with hydrazine. Specifically, the fluorescence of the probe was quenched due to the attached NN group, which can be reduced to -NH-NH- in the presence of hydrazine to turn on the fluorescence. The reduced intermediate can be easily oxidized in air to regenerate the original probe for recyclable usage. Both fluorometric and colorimetric readings were achieved by TLC with high sensitivity and excellent selectivity. This study thus represents a simple example of a reusable and naked-eye molecular probe for monitoring environmental hazards. Finally, the probe has also been applied to detect hydrazine in live cells.
Cheng, Xiamin,Zhang, Ruoyu,Cai, Xiaolei,Liu, Bin
p. 3565 - 3571
(2017/07/13)

Synthesis method for pharmaceutically acceptable salt of alkylhydrazine
The invention discloses a synthesis method for pharmaceutically acceptable salt of alkylhydrazine. According to the method, with hydrazine hydrate and BOC anhydride as starting raw materials, BOC hydrazine is synthesized firstly, then alkyl compounds are added in, BOC alkylhydrazine is obtained, finally BOC is removed, and the pharmaceutically acceptable salt of the corresponding alkylhydrazine is obtained in a conversion manner. According to the synthesis method, the raw materials for use are low in price and cost and easy to obtain. The synthesis method is short in synthesis route and high in yield, the obtained product is high in chemical purity, special production equipment is not needed for all reactions, and obtained intermediates and the final product do not need column chromatography and crystallization and purification.
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Paragraph 0036; 0039-0042

(2017/08/28)

Gold-catalyzed three-component spirocyclization: A one-pot approach to functionalized pyrazolidines
An efficient, highly atom economic synthesis of hitherto unknown spirocyclic pyrazolidines in a one-pot process was developed. The gold-catalyzed three-component coupling of alkynols, hydrazines and aldehydes or ketones likely proceeds via cycloisomerization of the alkynol to an exocyclic enol ether and subsequent [3 + 2]-cycloaddition of an azomethine ylide. A library of 29 derivatives with a wide range of functional groups was synthesized in up to 97% yield. With this new method, every position in the final product can be substituted which renders the method ideal for applications in combinatorial or medicinal chemistry.
Wagner, Bernd,Hiller, Wolf,Ohno, Hiroaki,Krause, Norbert
supporting information
p. 1579 - 1583
(2016/02/10)

Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker
In this work the five-step assembly of a peptidomimetic structurally resembling Prolyl-Prolyl-Proline tripeptide is reported. Proline units are mimicked by two pyrazolidine rings connected to trans-1,2-cyclopentanedicarboxylic acid. The Pro-Pro-Pro mimetic resembles a tri-l-proline unit but with increased lipophilicity and structural constraints imposed by the linker.
Vertesaljai, Peter,Lebedyeva, Iryna O.,Oliferenko, Alexander A.,Qi, Xin,Fu, Junjie,Ostrov, David A.,Asiri, Abdullah M.,Dennis Hall,Katritzky, Alan
p. 6653 - 6655
(2016/01/28)

STANNOUS FLUORESCENT PROBE
Rhodamine B derivative selectively chelates Sn2+ to act as a fluorescent probe.
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Page/Page column 6; 7

(2015/11/10)

New bifunctional metalloproteinase inhibitors: An integrated approach towards biological improvements and cancer therapy
The key role of some matrix metalloproteinases (MMPs) on several pathological processes, including carcinogenesis and tumor growth, makes the development of MMP inhibitors (MMPIs) an attractive approach for cancer therapy. We present herein an integrated approach for the development of a new series of inhibitors of MMP2 and MMP14, two enzymes over-expressed by human ovarian cancer. As a first step, a new series of single model compounds bearing different zinc-binding groups (ZBGs), such as carboxylic, hydroxamic acid, hydrazide and sulfonylhydrazide groups, were studied and revealed reasonably good capacity for the Zn(II) chelation in solution and for the MMP inhibition. Aimed at further reinforcing the biological activity of these MMPIs as anti-cancer agents, a selection of those models was extra-functionalized with benzothiazole (BTA), a group with recognized antitumor activity. Analysis of the results obtained for these bifunctional compounds, in particular the inhibitory activity against MMP2 and MMP14 as well as the anti-proliferative activity on the A2780 ovarian cancer cell line, allowed to understand the activity dependence on the type of ZBG, as well as the relevance of the BTA moiety. Overall, the evidenced BTA-associated activity improvements on enzyme inhibition and cell antiproliferactivity, combined with the hydrolytic stability revealed by the hydrazide group, suggest that these new bifunctional BTA-hydrazide derivatives should be taken in consideration for the development of new generations of MMPIs with anti-cancer activity.
Marques, Sérgio M.,Abate, Claudia C.,Chaves, Sílvia,Marques, Fernanda,Santos, Isabel,Nuti, Elisa,Rossello, Armando,Santos, M. Amélia
p. 188 - 202
(2013/10/01)

Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol
A series of N′1,N′3-dialkyl- N′1,N′3-di(alkylcarbonothioyl) malonohydrazides have been designed and synthesized as anticancer agents by targeting oxidative stress and Hsp70 induction. Structure-activity relationship (SAR) studies lead to the discovery of STA-4783 (elesclomol), a novel small molecule that has been evaluated in a number of clinical trials as an anticancer agent in combination with Taxol.
Chen, Shoujun,Sun, Lijun,Koya, Keizo,Tatsuta, Noriaki,Xia, Zhiqiang,Korbut, Timothy,Du, Zhenjian,Wu, Jim,Liang, Guiqing,Jiang, Jun,Ono, Mitsunori,Zhou, Dan,Sonderfan, Andrew
p. 5070 - 5076
(2013/09/12)

PROCESS FOR THE SYNTHESIS OF BETA-AMINOCARBONYLS
The present application provides processes and intermediates useful in the production of β- aminocarbonyl- or β-aminothiocarbonyl-containing compounds. Provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazone. Also provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazine. The present application further provides intermediate aminoisocyanate and iminoisocyanate compounds, and methods for synthesizing the starting hydrazone and hydrazine compounds.
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Page/Page column 00370

(2013/05/23)

Design, synthesis and antiviral activity of novel pyridazines
A series of pyridazines were prepared and evaluated for their anti-HIV activity. The new synthetic route involving a novel rearrangement reaction provided a practical method for the preparation of 5-hydroxypyridazines. The primary bioassay results indicated that most of the pyridazines possess anti-HIV activity. It ought to been mentioned that the rearranged compounds 35 and 39 exhibited relatively higher HIV inhibitory effect. Most of the synthesized compounds were also found to possess good anti-TMV activity, of which compound 9 showed similar in vivo anti-TMV activity to commercial plant virucide Ribavirin. This work provides a new and efficient approach to evolve novel multi-functional antiviral agents by rational integration and optimization of previously reported antiviral agents.
Wang, Ziwen,Wang, Mingxiao,Yao, Xue,Li, Yue,Tan, Juan,Wang, Lizhong,Qiao, Wentao,Geng, Yunqi,Liu, Yuxiu,Wang, Qingmin
scheme or table
p. 33 - 41
(2012/09/08)

PH-triggered blooming of 'nano-flowers' for tumor intracellular drug delivery
With the decrease in pH value, the 'nano-flower' exhibited a half-open state to expose the target ligands on the surface under tumor acidic conditions and fully bloomed to release Dox under endosomal acidic conditions.
Yuan, Zhefan,Que, Zhenyang,Cheng, Sixue,Zhuo, Renxi,Li, Feng
supporting information; experimental part
p. 8129 - 8131
(2012/09/11)

Design, synthesis, and evaluation of novel small molecule inhibitors of the influenza virus protein NS1
Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The existing vaccination program is variably effective from year to year, and drug resistance to available antivirals is a growing problem, making the development of additional antivirals an important challenge. Influenza virus non-structural protein 1 (NS1) is the centerpiece of the viral response to the host interferon (IFN) system. NS1 was demonstrated previously to be a potential therapeutic target for antiviral therapy by the identification of specific small-molecule inhibitors. One inhibitory compound, NSC125044, was subjected to chemical evaluation. Initial synthetic work comprised simplifying the core structure by removing unwanted functionality and determination of key features important for activity. Several subclasses of molecules were designed and synthesized to further probe activity and develop the basis for a structure-activity relationship. Apparent potency, as judged by activity in virus replication assays, increased dramatically for some analogs, without cytotoxicity. Results suggest that the target binding site tolerates hydrophobic bulk as well as having a preference for weakly basic substituents.
Jablonski, Joseph J.,Basu, Dipwanita,Engel, Daniel A.,Geysen, H. Mario
experimental part
p. 487 - 497
(2012/02/15)

Effective strategy for the systematic synthesis of hydrazine derivatives
A new and efficient strategy for the systematic synthesis of hydrazine derivatives is reported. It allows the synthesis of up to tetrasubstituted hydrazine derivatives with minimal number of steps using only one protecting group or without any of them at all. Simple and readily available starting materials such as hydrazine hydrate or phenylhydrazine can be used. A variety of substrates were used to investigate scope and limitations of this strategy, additionally one full synthetic sequence was performed.
Bredihhin, Aleksei,M?eorg, Uno
p. 6788 - 6793
(2008/12/20)

A selective method for cleavage of N-Troc-protected hydrazines and amines under mild conditions using mischmetal and TMSCI
The Troc (2,2,2-trichloroethoxycarbonyl) protecting group was efficiently removed under neutral conditions from corresponding protected hydrazines and amines using mischmetal in good to excellent yields. Two new substituted hydrazines were synthesised.
Vellemaee, Eerold,Lebedev, Oleg,Sillard, Rannar,Maeeorg, Uno
p. 685 - 687
(2007/10/03)

Aza-amino acid scan for rapid identification of secondary structure based on the application of N-Boc-aza1-dipeptides in peptide synthesis
Azapeptides, peptide analogues in which the α-carbon of one or more of the amino acid residues is replaced with a nitrogen atom, exhibit propensity for adopting β-turn conformations. A general protocol for the synthesis of azapeptides without racemization on solid phase has now been developed by introducing the aza-amino acid residue as an N-Boc-aza1-dipeptide. This approach has been validated by the synthesis of six N-Boc-aza 1-dipeptides and their subsequent introduction into analogues of the C-terminal peptide fragment of the human calcitonin gene-related peptide (hCGRP). By performing an aza-amino acid scan of such antagonist peptides, a set of aza-hCGRP analogues was synthesized to examine the relationship between turn secondary structure and biological activity.
Melendez, Rosa E.,Lubell, William D.
p. 6759 - 6764
(2007/10/03)

SYNTHESIS OF A NON-SYMMETRIC AZODICARBONYL COMPOUND AND ITS REGIOSELECTIVE REACTION WITH ORGANOMETALLIC REAGENTS
The non-symmetric azodicarbonyl compound 7 reacted with R-M/Lewis acid regioselectively at the nitrogen atom attached to the amide group giving 9, whereas it reacted with R-M at the nitrogen atom attached to the ester group producing 8 in high yield.
Yamamoto, Yoshinori,Yumoto, Masatoshi,Yamada, Jun-ichi
p. 3079 - 3082
(2007/10/02)

IMPROVED METHODS OF OBTAINING Nim-TRITYL-SUBSTITUTED HISTIDINE DERIVATIVES
Two variants are proposed for the synthesis of Nα-Boc-Nim-tritylhistidiine.The first variant starts from Nα,Nim-di-Boc-histidine, from which the Nim-Boc group is removed with hydrazine hydrate.The Nα-Boc-histidine formed is esterified with chlorotrimethylsilane, tritylated in the imidazole group, and, after the elimination of the trimethylsilyl protection from the carboxyl group, Nα-Boc-Nim-tritylglycine is obtained with a yield of 80percent.The second variant starts from Nα,Nim-ditritylhistidine, which, by treatment with hydrochloric acid in acetone and then with dilute ammonia, is converted into Nim- tritylhistidine.From this, by acylation with di-tert-butyl pyrocarbonate, Nα-Boc-Nim-tritylhistidine is obtained with a yield of 91percent.The acylation of Nim-tritylhistidine with other alkoxycarbonylating reagents leads to Nα-tert-amyl-, Nα-benzyl-, and Nα-4-methoxybenzyloxycarbonyl derivatives of Nim-tritylhistidine.
Pozdnev, V. F.
p. 322 - 327
(2007/10/02)