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Article ; Online: P(III)-Mediated Formal Reductive N-H Bond Insertion Reaction of Hydrazones to α-Keto Esters.

Takeda, Norihiko / Miyashita, Tomoki / Hirokawa, Naoya / Yasui, Motohiro / Ueda, Masafumi

2024 Volume 72, Issue 4, Page(s) 413–420

Abstract: A diazo-, metal-, and base-free multi-substituted hydrazone synthesis via a formal reductive N-H ... a broad substrate scope and good functional group tolerance, providing N-H bond insertion products ... in moderate to excellent yields. Moreover, P(III)-mediated N-H functionalization of pharmaceutical containing ...

Abstract	A diazo-, metal-, and base-free multi-substituted hydrazone synthesis via a formal reductive N-H bond insertion reactions of hydrazones to α-keto esters has been developed. The protocol features a broad substrate scope and good functional group tolerance, providing N-H bond insertion products in moderate to excellent yields. Moreover, P(III)-mediated N-H functionalization of pharmaceutical containing hydrazone moiety was also successfully achieved.
MeSH term(s)	Hydrazones/chemistry ; Hydrazones/chemical synthesis ; Esters/chemistry ; Esters/chemical synthesis ; Molecular Structure ; Oxidation-Reduction ; Ketones/chemistry ; Ketones/chemical synthesis ; Catalysis
Chemical Substances	Hydrazones ; Esters ; Ketones
Language	English
Publishing date	2024-04-27
Publishing country	Japan
Document type	Journal Article
ZDB-ID	213307-6
ISSN	1347-5223 ; 0009-2363
ISSN (online)	1347-5223
ISSN	0009-2363
DOI	10.1248/cpb.c24-00091
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Article: Surfactant-Assisted Synthesis of Pt Nanocubes Using Poly(N-isopropylacrylamide) Nanogels

Watanabe, Jun / Tanaka, Yoshiaki / Maeda, Yuusuke / Harada, Yusuke / Hirokawa, Yoshitsugu / Kawakita, Hidetaka / Ohto, Keisuke / Morisada, Shintaro

Langmuir. 2021 Sept. 29, v. 37, no. 40

2021

Abstract: Poly(N-isopropylacrylamide) (PNIPAM) nanogels were prepared by emulsion polymerization using ...

Abstract	Poly(N-isopropylacrylamide) (PNIPAM) nanogels were prepared by emulsion polymerization using sodium dodecyl sulfate (SDS) and employed as a capping agent in platinum nanoparticle (Pt NP) synthesis by liquid-phase reduction with hydrogen gas. When the PNIPAM nanogels were used without removing SDS, that is, a slight amount of SDS was included in the reaction solution, Pt nanocubes (NCs) were predominantly produced (>80%). The proportion of the resultant Pt NCs was much higher than that obtained using the PNIPAM linear polymer (∼60%). To clarify the effects of the three-dimensional polymer network and SDS, we synthesized Pt NPs using the PNIPAM nanogel without SDS (SDS-free PNIPAM nanogel) and found that Pt NCs are rarely formed, and most NPs obtained have an irregular shape. When only SDS was used as a capping agent, NCs were hardly obtained, but other polyhedral NPs were formed. Furthermore, the use of SDS together with the PNIPAM polymer led to the decrease in the proportion of the Pt NCs compared with that obtained using only the linear polymer. These results indicate that the enhancement of the Pt NC proportion using the PNIPAM nanogel with SDS is attributable to not only the three-dimensional polymer network of the PNIPAM nanogel but also the assist of SDS as a capping agent.
Keywords	emulsions ; hydrogen ; nanogels ; platinum ; polymerization ; polymers ; sodium dodecyl sulfate
Language	English
Dates of publication	2021-0929
Size	p. 11859-11868.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	2005937-1
ISSN	1520-5827 ; 0743-7463
ISSN (online)	1520-5827
ISSN	0743-7463
DOI	10.1021/acs.langmuir.1c01873
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Article ; Online: Highly Diastereoselective Synthesis of 2-(1-N-Boc-aminoalkyl)thiazole-5-carboxylates by Reduction of tert-Butylsulfinyl Ketimines.

Magata, Takuji / Hirokawa, Yoshimi / Furokawa, Aya / Takeuchi, Kazuhisa / Ohtomo, Yoshiaki / Kino, Toshitaka / Kominami, Jun / Nakai, Yuto / Kitamura, Maria / Maezaki, Naoyoshi

Chemical & pharmaceutical bulletin

2018 Volume 66, Issue 4, Page(s) 416–422

Abstract: Positional isomers of naturally occurring peptide subunits were synthesized via highly diastereoselective reduction of tert-butylsulfinyl ketimines as a key reaction. While ... ...

Abstract	Positional isomers of naturally occurring peptide subunits were synthesized via highly diastereoselective reduction of tert-butylsulfinyl ketimines as a key reaction. While NaBH
MeSH term(s)	Imines/chemistry ; Molecular Structure ; Nitriles/chemistry ; Oxidation-Reduction ; Stereoisomerism ; Thiazoles/chemical synthesis ; Thiazoles/chemistry
Chemical Substances	Imines ; Nitriles ; Thiazoles ; ketimine
Language	English
Publishing date	2018
Publishing country	Japan
Document type	Journal Article
ZDB-ID	213307-6
ISSN	1347-5223 ; 0009-2363
ISSN (online)	1347-5223
ISSN	0009-2363
DOI	10.1248/cpb.c17-00907
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Article: The KIF3 motor transports N-cadherin and organizes the developing neuroepithelium.

Teng, Junlin / Rai, Tatemitsu / Tanaka, Yosuke / Takei, Yosuke / Nakata, Takao / Hirasawa, Motoyuki / Kulkarni, Ashok B / Hirokawa, Nobutaka

Nature cell biology

2005 Volume 7, Issue 5, Page(s) 474–482

Abstract: ... for the Kap3 gene, we show that post-Golgi transport of N-cadherin by the KIF3 molecular motor complex is ... crucial for maintaining this balance. N-cadherin and beta-catenin associate with the KIF3 complex ... localization of N-cadherin was disrupted. Taken together, these results suggest a potential tumour-suppressing ...

Abstract	In the developing brain, the organization of the neuroepithelium is maintained by a critical balance between proliferation and cell-cell adhesion of neural progenitor cells. The molecular mechanisms that underlie this are still largely unknown. Here, through analysis of a conditional knockout mouse for the Kap3 gene, we show that post-Golgi transport of N-cadherin by the KIF3 molecular motor complex is crucial for maintaining this balance. N-cadherin and beta-catenin associate with the KIF3 complex by co-immunoprecipitation, and colocalize with KIF3 in cells. Furthermore, in KAP3-deficient cells, the subcellular localization of N-cadherin was disrupted. Taken together, these results suggest a potential tumour-suppressing activity for this molecular motor.
MeSH term(s)	Adaptor Proteins, Signal Transducing/genetics ; Adaptor Proteins, Signal Transducing/metabolism ; Animals ; Brain/embryology ; Brain/physiology ; Cadherins/metabolism ; Cell Adhesion/genetics ; Cell Adhesion/physiology ; Cell Differentiation/genetics ; Cell Differentiation/physiology ; Cell Transformation, Neoplastic/genetics ; Cell Transformation, Neoplastic/pathology ; Cells, Cultured ; Cytoskeletal Proteins/genetics ; Cytoskeletal Proteins/metabolism ; Golgi Apparatus/metabolism ; Mice ; Molecular Motor Proteins/genetics ; Molecular Motor Proteins/metabolism ; Morphogenesis/physiology ; Neuroepithelial Cells/cytology ; Neuroepithelial Cells/metabolism ; Neurons/cytology ; Neurons/physiology ; Trans-Activators/metabolism ; beta Catenin
Chemical Substances	Adaptor Proteins, Signal Transducing ; CTNNB1 protein, mouse ; Cadherins ; Cytoskeletal Proteins ; Molecular Motor Proteins ; Trans-Activators ; beta Catenin ; Kifap3 protein, mouse (180856-77-3)
Language	English
Publishing date	2005-05
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1474722-4
ISSN	1476-4679 ; 1465-7392
ISSN (online)	1476-4679
ISSN	1465-7392
DOI	10.1038/ncb1249
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Zs.A 5169: Show issues			Location: Je nach Verfügbarkeit (siehe Angabe bei Bestand) bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular Jg. 1995 - 2021: Lesesall (2.OG) ab Jg. 2022: Lesesaal (EG)
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Article ; Online: Impaired myocardial blood flow reserve in subjects with metabolic syndrome analyzed using positron emission tomography and N-13 labeled ammonia.

Teragawa, Hiroki / Morita, Koichi / Shishido, Hiroki / Otsuka, Nobuaki / Hirokawa, Yutaka / Chayama, Kazuaki / Tamaki, Nagara / Kihara, Yasuki

European journal of nuclear medicine and molecular imaging

2009 Volume 37, Issue 2, Page(s) 368–376

Abstract: ... response in MS subjects using N-13 labeled ammonia and positron emission tomography.: Methods and results ... Myocardial blood flow (MBF) was measured at rest and during adenosine infusion in MS subjects (n = 13, MS ... group) with no definite evidence of heart disease and in subjects without MS (n = 14, non-MS group ...

Abstract	Purpose: Coronary vasomotor response might be impaired in metabolic syndrome (MS); however, the precise abnormality has not been elucidated. The aim of this study was to assess coronary-vasomotor response in MS subjects using N-13 labeled ammonia and positron emission tomography. Methods and results: Myocardial blood flow (MBF) was measured at rest and during adenosine infusion in MS subjects (n = 13, MS group) with no definite evidence of heart disease and in subjects without MS (n = 14, non-MS group). Coronary vascular resistance (CVR) was calculated by dividing the mean aortic blood pressure by MBF. Myocardial blood flow reserve (MFR) was calculated as the ratio of the MBF during adenosine infusion to that during rest. Blood chemical parameters were measured to evaluate their relationship with MFR. During adenosine infusion, MBF was lower (p = 0.0085) and CVR higher (p = 0.0128) in the MS group than in the non-MS group and MFR was significantly lower in the MS group than in the non-MS group (2.13 +/- 0.99 vs. 3.38 +/- 0.95, p = 0.0027). Multivariate analysis demonstrated that the homeostasis model assessment-insulin resistance (p < 0.05) and the presence of hypertension (p < 0.05) were independent determinants of MFR. Conclusions: The results indicate that MFR was impaired in MS subjects, suggesting that an abnormal coronary microvascular response occurred in these subjects. This abnormality may have been partially due to insulin resistance and hypertension.
MeSH term(s)	Ammonia ; Coronary Circulation ; Coronary Vessels/physiopathology ; Humans ; Male ; Metabolic Syndrome/diagnostic imaging ; Metabolic Syndrome/physiopathology ; Middle Aged ; Nitrogen Radioisotopes ; Positron-Emission Tomography ; Retrospective Studies ; Tomography, X-Ray Computed ; Ultrasonography
Chemical Substances	Nitrogen Radioisotopes ; Ammonia (7664-41-7)
Language	English
Publishing date	2009-11-14
Publishing country	Germany
Document type	Journal Article
ZDB-ID	8236-3
ISSN	1619-7089 ; 0340-6997 ; 1619-7070
ISSN (online)	1619-7089
ISSN	0340-6997 ; 1619-7070
DOI	10.1007/s00259-009-1307-6
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Zs.A 1227: Show issues

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Article ; Online: Successful Premedication With Sublingual Midazolam Using a Suction Toothbrush.

Hirokawa, Jun / Kimata, Naomi

Anesthesia progress

2023 Volume 70, Issue 2, Page(s) 80–84

Abstract: Premedication is often used to reduce the stress associated with anesthesia-related procedures. However, in some cases, patients may not cooperate with medication delivery because of significant fear and anxiety. We report a case of an uncooperative ... ...

Abstract	Premedication is often used to reduce the stress associated with anesthesia-related procedures. However, in some cases, patients may not cooperate with medication delivery because of significant fear and anxiety. We report a case of an uncooperative patient with severe intellectual disabilities who was successfully premedicated with the unique technique of sublingual midazolam administration using a suction toothbrush. The 38-year-old male patient was planned to receive dental treatment under deep intravenous sedation (IVS), but he refused both intravenous cannulation and mask induction. Preanesthetic medication delivery using other routes was attempted but not accepted. As the patient tolerated toothbrushing, we used repeated practice with sublingual water administration through the toothbrush's suction hole to gradually desensitize the patient. Using that same method, sublingual midazolam was administered as a successful premedication to allow placement of a face mask for inhalational induction without distress and completion of the dental treatment under IVS. For patients who refuse other premedication routes, sublingual administration during toothbrushing with a suction toothbrush may provide a successful alternative.
MeSH term(s)	Male ; Humans ; Adult ; Midazolam ; Administration, Sublingual ; Toothbrushing ; Suction ; Premedication ; Preanesthetic Medication/methods ; Anesthesia, General ; Double-Blind Method ; Hypnotics and Sedatives
Chemical Substances	Midazolam (R60L0SM5BC) ; Hypnotics and Sedatives
Language	English
Publishing date	2023-06-28
Publishing country	United States
Document type	Case Reports ; Journal Article
ZDB-ID	603800-1
ISSN	1878-7177 ; 0003-3006
ISSN (online)	1878-7177
ISSN	0003-3006
DOI	10.2344/anpr-70-01-05
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Article: Design, synthesis, and biological activity of non-amidine factor Xa inhibitors containing pyridine N-oxide and 2-carbamoylthiazole units.

Haginoya, Noriyasu / Kobayashi, Syozo / Komoriya, Satoshi / Yoshino, Toshiharu / Nagata, Tsutomu / Hirokawa, Yumiko / Nagahara, Takayasu

Bioorganic & medicinal chemistry

2004 Volume 12, Issue 21, Page(s) 5579–5586

Abstract: ... FXV673, we synthesized a series of thiazol-5-ylpyridine derivatives containing pyridine N-oxide and 2 ... carbamoylthiazole units to optimize the S4 binding element. N-Oxidation of thiazol-5-ylpyridine increased the anti ... fXa activity more than 10-fold independent on the position of N-oxide. The 4-pyridine N-oxide ...

Abstract	Based on the both of results for X-ray studies of tetrahydrothiazolopyridine derivative 1c and FXV673, we synthesized a series of thiazol-5-ylpyridine derivatives containing pyridine N-oxide and 2-carbamoylthiazole units to optimize the S4 binding element. N-Oxidation of thiazol-5-ylpyridine increased the anti-fXa activity more than 10-fold independent on the position of N-oxide. The 4-pyridine N-oxide derivatives 3a and 3d excelled over the tetrahydrothiazolopyridine 1b in potency. 2-Methylpyridine N-oxide 3d exhibited 49-fold selectivity over thrombin. Our modeling study proposed a binding mode that the pyridine N-oxide ring of 3a stuck into the "cation hole" , and the oxide anion of 3a occupied in the almost same space to that of FXV673. From observations of the SAR and modeling studies, we suggested the possibilities that the formation of hydrogen bond with the oxide anion in the "cation hole" and the affinity of cationic pyridine ring to S4 subsite were responsible for increase in anti-fXa activity.
MeSH term(s)	Amidines/chemical synthesis ; Amidines/pharmacology ; Animals ; Binding Sites/physiology ; Cyclic N-Oxides/chemical synthesis ; Cyclic N-Oxides/pharmacology ; Drug Design ; Factor Xa/metabolism ; Factor Xa Inhibitors ; Humans ; Male ; Pyridines/chemical synthesis ; Pyridines/pharmacology ; Rats ; Rats, Wistar ; Serine Proteinase Inhibitors/chemical synthesis ; Serine Proteinase Inhibitors/pharmacology ; Thiazoles/chemical synthesis ; Thiazoles/pharmacology
Chemical Substances	Amidines ; Cyclic N-Oxides ; Factor Xa Inhibitors ; Pyridines ; Serine Proteinase Inhibitors ; Thiazoles ; Factor Xa (EC 3.4.21.6)
Language	English
Publishing date	2004-11-01
Publishing country	England
Document type	Journal Article
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2004.08.001
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Zs.A 3815: Show issues

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Article: A novel series of N-(hexahydro-1,4-diazepin-6-yl) and N-(hexahydroazepin- 3-yl)benzamides with high affinity for 5-HT3 and dopamine D2 receptors.

Hirokawa, Y / Morie, T / Yamazaki, H / Yoshida, N / Kato, S

Bioorganic & medicinal chemistry letters

1998 Volume 8, Issue 6, Page(s) 619–624

Abstract: A novel series of benzamides with a hexahydro-1,4-diazepine or hexahydroazepine ring in the amine moiety were prepared, and their binding affinities for 5-HT3 and dopamine D2 receptors were evaluated. The R isomer of the 1-ethyl-4-methylhexahydro-1,4- ... ...

Abstract	A novel series of benzamides with a hexahydro-1,4-diazepine or hexahydroazepine ring in the amine moiety were prepared, and their binding affinities for 5-HT3 and dopamine D2 receptors were evaluated. The R isomer of the 1-ethyl-4-methylhexahydro-1,4-diazepinylbenzamide (R)-22 had potent affinity for both receptors. The R-enantiomer of the corresponding 1-ethylhexahydroazepinylbenzamide 28 showed potent affinity for dopamine D2 receptors with reduced affinity for 5-HT3 receptors, while the S isomer was found to be a potent and selective 5-HT3 receptor antagonist.
MeSH term(s)	Animals ; Benzamides/metabolism ; Binding Sites ; Cerebral Cortex/metabolism ; Corpus Striatum/metabolism ; Domperidone/metabolism ; Dopamine Antagonists/metabolism ; Imidazoles/metabolism ; Indoles/metabolism ; Ligands ; Metoclopramide/metabolism ; Models, Chemical ; Ondansetron/metabolism ; Rats ; Receptors, Dopamine D2/metabolism ; Receptors, Serotonin/metabolism ; Receptors, Serotonin, 5-HT3 ; Serotonin Antagonists/metabolism ; Spiperone/metabolism ; Stereoisomerism
Chemical Substances	Benzamides ; Dopamine Antagonists ; Imidazoles ; Indoles ; Ligands ; Receptors, Dopamine D2 ; Receptors, Serotonin ; Receptors, Serotonin, 5-HT3 ; Serotonin Antagonists ; GR 65630 (117186-80-8) ; Ondansetron (4AF302ESOS) ; Spiperone (4X6E73CJ0Q) ; Domperidone (5587267Z69) ; Metoclopramide (L4YEB44I46)
Language	English
Publishing date	1998-03-17
Publishing country	England
Document type	Journal Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/s0960-894x(98)00078-x
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Zs.A 3203: Show issues

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Book ; Online: Compositional Confluence Criteria

Shintani, Kiraku / Hirokawa, Nao

2023

Abstract: We show how confluence criteria based on decreasing diagrams are generalized to ones composable with other criteria. For demonstration of the method, the confluence criteria of orthogonality, rule labeling, and critical pair systems for term rewriting ... ...

Abstract	We show how confluence criteria based on decreasing diagrams are generalized to ones composable with other criteria. For demonstration of the method, the confluence criteria of orthogonality, rule labeling, and critical pair systems for term rewriting are recast into composable forms. We also show how such a criterion can be used for a reduction method that removes rewrite rules unnecessary for confluence analysis. In addition to them, we prove that Toyama's parallel closedness result based on parallel critical pairs subsumes his almost parallel closedness theorem. Comment: 28 pages, 3 figures, 1 table, submitted to LMCS
Keywords	Computer Science - Logic in Computer Science
Publishing date	2023-03-07
Publishing country	us
Document type	Book ; Online
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Article: Reaction-Induced Self-Assembly of Gel Structure: A New Insight into Chemical Gelation Process of N-Isopropylacrylamide as Studied by Two-Dimensional Infrared Correlation Spectroscopy

Park, Yeonju / Hashimoto Chihiro / Hashimoto Takeji / Hirokawa Yoshitsugu / Jung Young Mee / Ozaki Yukihiro

Macromolecules. 2013 May 14, v. 46, no. 9

2013

Abstract: We report a new insight into the chemical gelation process of poly(N-isopropylacrylamide) (PNiPAAm ...

Abstract	We report a new insight into the chemical gelation process of poly(N-isopropylacrylamide) (PNiPAAm) hydrogel elucidated on the basis of the in situ observations with time-resolved Fourier-transform infrared spectroscopy (FTIR), its principal component analysis (PCA), and two-dimensional correlation spectroscopy (2D COS) at preparation temperatures below and above the lower critical solution temperature of PNiPAAm aqueous solution. First, we spectroscopically identified for the first time the specific time-spans for the two-stage reaction process: the first-stage giving rise to linear and branched random copolymers of NiPAAm and cross-linker monomers and the second-stage giving rise to cross-linking into macroscopic network structure. Second, we conducted 2D COS for both the first-stage and second-stage reaction processes in order to resolve highly superposed spectra in the amide I and II regions into fundamental spectra comprising the superposed spectra. We elucidated the time-sequence order of the changes in the fundamental spectra occurring in situ during the gelation process. We proposed molecular interpretations of the sequence of the spectroscopic events, which would give deep insights into molecular mechanisms of the gelation process as detailed in the text.
Keywords	aqueous solutions ; composite polymers ; crosslinking ; Fourier transform infrared spectroscopy ; gelation ; hydrogels ; principal component analysis ; temperature
Language	English
Dates of publication	2013-0514
Size	p. 3587-3602.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	1491942-4
ISSN	1520-5835 ; 0024-9297
ISSN (online)	1520-5835
ISSN	0024-9297
DOI	10.1021%2Fma400457e
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