Effects of a novel non-steroidal anti-inflammatory drug (M-5011) on bone metabolism in rats with collagen-induced arthritis

Murakami, Naofumi; Takase, Hiroshi; Saitô, Takako; Iwata, Kazuo; Miura, Hiroaki; Naruse, Tomofumi

doi:10.1016/s0014-2999(98)00342-2

Cited by 16 publications

(12 citation statements)

References 27 publications

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“…1 Currently, there is no curative treatment for the disease, 2 and the medications available, ie, analgesics or nonsteroidal anti-inflammatory drugs, 3 disease-modifying antirheumatic drugs, biological therapy, 4 and glucocorticoids, only mitigate its symptomatology. 5 Glucocorticoids are the most powerful anti-inflammatory drugs known, and inhibit migration of leukocytes to sites of inflammation by decreasing or inhibiting the action of some of the chemical mediators of inflammation.…”

Section: Introductionmentioning

confidence: 99%

Development of biodegradable methylprednisolone microparticles for treatment of articular pathology using a spray-drying technique

Tobar-Grande¹,

Godoy²,

Bustos³

et al. 2013

IJN

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Abstract:In this work, microparticles were prepared by spray-drying using albumin, chondroitin sulfate, and hyaluronic acid as excipients to create a controlled-release methylprednisolone system for use in inflammatory disorders such as arthritis. Scanning electron microscopy demonstrated that these microparticles were almost spherical, with development of surface wrinkling as the methylprednisolone load in the formulation was increased. The methylprednisolone load also had a direct influence on the mean diameter and zeta potential of the microparticles. Interactions between formulation excipients and the active drug were evaluated by x-ray diffraction, differential scanning calorimetry, and thermal gravimetric analysis, showing limited amounts of methylprednisolone in a crystalline state in the loaded microparticles. The encapsulation efficiency of methylprednisolone was approximately 89% in all formulations. The rate of methylprednisolone release from the microparticles depended on the initial drug load in the formulation. In vitro cytotoxic evaluation using THP-1 cells showed that none of the formulations prepared triggered an inflammatory response on release of interleukin-1β, nor did they affect cellular viability, except for the 9.1% methylprednisolone formulation, which was the maximum test concentration used. The microparticles developed in this study have characteristics amenable to a therapeutic role in inflammatory pathology, such as arthritis.

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Section: Introductionmentioning

confidence: 99%

Development of biodegradable methylprednisolone microparticles for treatment of articular pathology using a spray-drying technique

Tobar-Grande¹,

Godoy²,

Bustos³

et al. 2013

IJN

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“…The thiophene moiety is present in a large number of bioactive molecules having diverse biological activities such as anti-inflammatory (Murakami et al, 1998), anticonvulsant (Kulandasamy et al, 2009), antibacterial (Lu et al, 2011) and antitumor (Kaushik et al, 2012). The quinoline ring system is one of the most commonly encountered heterocycles in medicinal chemistry (Bouraiou et al, 2007).…”

Section: Structure Descriptionmentioning

confidence: 99%

Ethyl 8-amino-7-(furan-2-yl)-5,6-dihydrothieno[2,3-b]benzo[h]quinoline-9-carboxylate

Bakhite¹,

Kaur²,

Akkurt³

et al. 2016

IUCr Data

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In the title compound, C 22 H 18 N 2 O 3 S, the two independent molecules in the asymmetric unit form a dimer via N-HÁ Á ÁO hydrogen bonds. In the crystal, the molecular layers can be found in the (110) plane, connected by C-HÁ Á Á interactions. Atoms of the furan ring of one independent molecule are disordered over two sets of sites with an occupancy ratio 0.735 (3):0.265 (3). Structure descriptionThe thiophene moiety is present in a large number of bioactive molecules having diverse biological activities such as anti-inflammatory (Murakami et al., 1998), anticonvulsant (Kulandasamy et al., 2009), antibacterial (Lu et al., 2011) and antitumor (Kaushik et al., 2012. The quinoline ring system is one of the most commonly encountered heterocycles in medicinal chemistry (Bouraiou et al., 2007). Substituted quinolines possess diverse chemotherapeutic activities including antibacterial (Kidwai et al., 2000), antifungal (Musiol et al., 2006), antimalarial (Charris et al., 2005Cunico et al., 2006) and antitumor (Chen et al., 2006). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound.In the asymmetric unit (Fig. 1), the two independent molecules A and B form a dimer via N-HÁ Á ÁO hydrogen bonds (Table 1). In both molecules, the cyclohexene rings of the fused tetracyclic cores are puckered with Q T = 0.438 (2) Å , = 65.0 (2) , ' = 277.0 (3) in A and Q T = 0.481 (2) Å , = 111.8 (2) , ' = 87.2 (2) in B. In both A and B, the molecular conformation is stabilized by an N-HÁ Á ÁO hydrogen bonds. In the crystal, molecular layers can be found in the (110) plane which are connected by C-HÁ Á Á and C-HÁ Á ÁN interactions (Fig. 2, Table 1). There is a -interaction between the N1A/C4A-C8A and C9A-C14A(Àx, Ày + 1, Àz + 2) rings with a centroid-centroid distance of 3.7975 (10) Å . Synthesis and crystallization RefinementCrystal data, data collection and structure refinement details are summarized in Table 2. Atoms O3/C17-C20 atoms of the furan ring of molecule A are disordered over two sets of sites with an occupancy ratio 0.735 (3):0.265 (3).

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“…Thiophene moiety is present in a large number of bioactive molecules having diverse biological activities such as anti-inflammatory [1], anticonvulsant [2], antibacterial [3], and antitumor activities [4]. Moreover, thiophene moiety is a well known as isostere for benzene; for example, the replacement of benzene ring of the antidepressant drug, Viloxazine (I, Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New Heterocyclic Compounds Containing Thienylbenzo[h]Quinoline Moiety

Al‐Taifi

Abbady

Bakhite

2015

Journal of Heterocyclic Chem

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In this paper the reaction of 2‐(2′‐thienylmethylene)‐3,4‐dihydronaphthalen‐2(1H)‐one (1) with cyanothioacetamide gave a mixture of 3‐cyano‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]quinolin‐2(1H)‐thione (2) and the related disulfide 3. Compound 2 was reacted with some halo compounds namely; ethyl chloroacetate, chloroacetamide, chloro(N‐(p‐chlorophenyl))acetamide, N1‐chloroacetylsulfanilamide, and 2‐chloromethyl‐1H‐benzimidazole to produce a series of 2‐(substituted)methylthio‐3‐cyano‐5,6‐dihydro‐4‐(2′‐thienyl)benzo[h]quinolines 4a, 4b, 4c, 4d, 4e and 11. Upon heating the latter compounds with sodium ethoxide, they underwent intramolecular Thorpe–Zeigler cyclization to furnish the corresponding 2‐(substituted)‐3‐amino‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]thieno[2,3‐b]quinolines 5a, 5b, 5c, 5d, 5e and 12. (3‐Cyano‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]quinolin‐2‐ylthio)acethydrazide (8) and the related isomer, 3‐amino‐5,6‐dihydro‐4‐(2′‐thienyl)thieno[2,3‐b]benzo[h]quinoline‐2‐carbohydrazide (9), were also synthesized. Most of the aforementioned compounds were used as key intermediates for synthesizing other benzo[h]quinolines, benzo[h]thieno[2,3‐b]quinolines as well as benzo[h]pyrimido[4′,5′:4,5] thieno[2,3‐b]quinolines. The structure of all synthesized compounds was confirmed by spectroscopic measurements and analytical analyses.

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Effects of a novel non-steroidal anti-inflammatory drug (M-5011) on bone metabolism in rats with collagen-induced arthritis

Cited by 16 publications

References 27 publications

Development of biodegradable methylprednisolone microparticles for treatment of articular pathology using a spray-drying technique

Development of biodegradable methylprednisolone microparticles for treatment of articular pathology using a spray-drying technique

Ethyl 8-amino-7-(furan-2-yl)-5,6-dihydrothieno[2,3-b]benzo[h]quinoline-9-carboxylate

Synthesis and Characterization of New Heterocyclic Compounds Containing Thienylbenzo[h]Quinoline Moiety

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