• Title/Summary/Keyword: 4-Amino-2

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Synthesis of (${\pm}$)-cis-8-amino-l-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno [1,2-b][1,4]oxazine ((${\pm}$)-cis-8-Amino-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno [1,2-b][1,4]oxazine의 합성)

  • Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.52 no.6
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    • pp.488-493
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    • 2008
  • 2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine D3 agonist with low neurotoxicity. Dopamine D3 agonist was evaluated as selective for the treatment of Parkinson's disease. In order to develop a novel dopamine D3 agonist, we tried to synthesize the aminothiazoloindenoxazine derivative that is a hybrid structure of aminoindenoxazine and thiazole ring. cis-2-Amino-1-indanol (2) was synthesized from 1,2-indandione-2-oxime by catalytic hydrogenation and it was treated with chloroacetyl chloride and NaH in benzene solution to give (${\pm}$)-cis-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one (6). Nitration of 6 by the mixed acid gave 8-nitro compound (7) and the carbonyl group of 7 was reduced with $LiAlH_4$ to afford compound (8). 8 was reduced to form (${\pm}$)-cis-8-amino-2,3,4,4a,5,9b-hexahydroindeno[1,2-b][1,4]oxazine (9) and finally it was cyclized with KSCN in glacial acetic acid to yield (${\pm}$)-cis-8-amino-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno[1,2-b][1,4]oxazine (10).

A Highly Stereoselective Synthesis and Crystal Structure of (E)-4'-Amino-3,4,5- trimethoxystilbene ((E)-4'-Amino-3,4,5-trimethoxystilbene의 선택적인 합성 및 결정 구조)

  • Li, Xia-Bing;Zhang, Xi-Quan;Gu, Hong-Mei;Li, Bao-Lin
    • Journal of the Korean Chemical Society
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    • v.55 no.2
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    • pp.251-255
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    • 2011
  • A new and highly stereoselective synthesis of (E)-4'-amino-3,4,5-trimethoxystilbene was achieved by using 3,4,5-trimethoxybenzaldehyde and p-nitrotoluene as starting materials through condensation under solvent-free condition and followed by the reducing of nitro group with the system of $NH_2NH_2/FeCl_3$/C in ethanol. The crystal structure of (E)-4'-amino-3,4,5-trimethoxystilbene was also determined by X-ray diffraction analysis.

Synthesis of 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (6-Amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan의 합성)

  • Kim, Min-Kyeom;Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.52 no.1
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    • pp.20-26
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    • 2008
  • 2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. Selenium was reported to have an improved antioxidant ability and to reduce the loss of dopamine. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine agonist with low neurotoxocity. In order to develop a novel dopamine agonist, we tried to synthesize the selenazoloaminoindan derivative that is a hybrid structure of aminoindan and aminoselenazole instead of aminothiazole. 2-Indanone-2-oxime was reduced with $TiCl_4$ and $NaBH_4$ to form 2-aminoindan, which was reacted with propionyl chloride to give 2-N-n-propionylaminoindan (2). Compound 2 was reduced with $TiCl_4$ and $NaBH_4$ to afford 2-N-n-propylaminoindan (3) and it was nitrated and reduced to form 5-amino-2-N-n-propylaminoindan (5), which was reacted with KSeCN, $Br_2$, and glacial acetic acid to give 4,6-dibromo-5- amino-2-N-n-propylaminoindan (7) instead of selenazole ring formation. Otherwise, compound 2 was nitrated and hydrogenated to form 5-amino-2-N-n-propionylaminoindan (9), which was treated with KSeCN, $Br_2$, and glacial acetic acid to give 4,6-dibromo-5-amino-2-N-n-propionylaminoindan (10). Compound 9 was cyc1ized with KSeCN and glacial acetic acid in the absence of $Br_2$ to give 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (11).

A Study on the Amino Acid Contents of Edible Mushrooms (식용(食用)버섯류(類)의 아미노산(酸)에 관(關)한 연구(硏究))

  • Pyo, Myoung-Yun;Ro, Ihl-Hyeob
    • Journal of Nutrition and Health
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    • v.8 no.1
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    • pp.47-59
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    • 1975
  • Free amino acids in extracts and total amino acids in hydrolysates of eleven species of edible mushrooms were analyzed by amino acid autoanalyzer (Technicon PNC-1 Type). All these 11 species of mushroom can be repesented for convenience sake as follows. S-1; Agaricus campestris Fr. S-2: Agaricus campestris S-3; Pholiota nameko(I. Ito) S. Ito et Imai S-4; Auricularia auricula-judae(Fr.) $Qu{\acute{e}}l$ S-5; Tremella fuciformis Berk. S-6; Tricholoma matsutake(S. Ito et Imai) Sing. S-7; Pleurotus ostreatus Fr. $Qu{\acute{e}}l$ S-8; Lentinus edodes Berk Sing. S-9; Ramaria botrytis (Pers.) Ricken S-10; Coprinus comatus(Fr.) S.F, Gray S-11; Gyrophora esculenta The results obtained from this study are as follows. 1) 17 kinds of amino acid, including 7 kinds of essential amino acid in human nutrition except tryptophan were identified and quantified. 2) Of all free amino acids contained in mushrooms, glutamic acid is the richest, and then comes Ala, Thr, Pro and Lys in that order. There were no found Cys'and His in S-9;His in S-1; Met and Arg in S-11; Cys and Met in S-5;Pro, Cys, Met, Lys and Arg in S-4. Of all total amino acids which are closely related with nutritional valuation, glutamic acid is the richest, and then comes Asp, Ala, Arg, Leu, Thr, Gly in that order. Especially S-1 and S-2 contain high quantity $o{\acute{i}}$ proline in both free and total amino acids. 3) Cotents of ammonia in extracts of mushrooms in decreasing order in S-1, S-10, S-8, S-2, S-7, S-6, and S-2, S-6, S-8, S-9, S-1 in hydrolysates of mushrooms. 4) Gross Contents of free amino acid in extracts is high in decreasing order in S-10, S-1, S-7, S-6, S-8, and total amino acid in hydrolysates is high in S-10, S-2, S-2, S-8, S-1, S-9, S-6. 5) Besides 17 kinds of amino acid, 5 kinds of unknown amino acid are found in extracts and hydrolysates.

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The Study on the Characteristics of Commercial Samjangs (시판 쌈장의 품질 특성)

  • 서정숙;이택수;신동빈
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.30 no.3
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    • pp.382-387
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    • 2001
  • Characteristics of six commercial samjangs were analyzed such as proximate composition, free amino acids, organic acids and free sugars. Also color, taste and odor were evaluated by 36 panelists. They were composed of moisture content 41.4-48.4%, crude protein 9.2-10.4%, crude fat 2.2-3.4%, pH 5.3-5.7, amino nitrogen 194.0%-375.6 mg% and sodium chloride 7.7-9.1%. Total free amino acids of samjangs were 975.89-2304.98 mg%. Glutamic acid was the highest amino acid among free amino acids as 231.7-788.01 mg%. Proline, arginine, alanine and lysine were higher than other free amino acids while histidine, cystine and methionine were lower than other. Eleven free amino acids including glutamic acid were the highest in samjang (B) which contained more doenjang than any other makers did. Total organic acids were 401.01-640.27 mg%. 69.65-269.07 mg% of succinic acid was the highest among organic acids. Lactic acid was the highest in samjang (F) which was home made. Total free sugars was the highest in samjang (A) which contained more wheat flour than any other makers did it. Glucose was 9.30-23.99% and fructose was nd-2.69%. The result of proximate composition showed a different pattern comparing with that sensory evaluation. Samjang (A) which contained less salt showed the highest overall acceptability while samjang (F) which contained more dark color, more salt was the lowest one among the samples.

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甘味劑의 合成

  • Seong Jwa Gyeong
    • Journal of the Korean Chemical Society
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    • v.1 no.1
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    • pp.20-22
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    • 1949
  • 最近 2-Amino-1-nitrophenol 및 Alkyl ether의 甘味에 對한 News가 傳하여지고 있어 特히 n-Propylether는 의 4,000培의 甘味를 가졌다고한다. 本報에서는 그 合成條件을 檢사하였다. 同時에 2-Amino-4-nitro-toluene 2-Amino-4-nitro benzoic acid를 合成하여 그 甘味를 試驗하였다.

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An Alternate Synthesis of 2-Amino-5,6-dimethoxy-1,2,3,4-Tetrahydronaphthalene Hydrochloride (2-아미노-5,6-디메톡시-1,2,3,4-테트라히드로나프탈렌 염화히드로의 합성)

  • Jack C. Kim;Suk-kee Lee;Chang-bae Kim;Suk-kyu Han;Soon-kyu Choi;Kyung-hee Lee
    • Journal of the Korean Chemical Society
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    • v.21 no.3
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    • pp.187-192
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    • 1977
  • An alternate synthesis of 2-amino-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene hydrochloride from 2-nitro-3,4-dihydro-5,6-dimethoxy-1(2H)-naphthalenone,was described and compared the overall yields and experimental procedures with the previous synthetic routes obtained from Neber rearrangement product, 2-amino-3,4-dihydro-5,6-dimethoxy-1(2H)-naphthalenone hydrochloride.

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The Synthesis and Properties of Asymmetrically Substituted 4,4'-Bis(1,3,5-triazine-6-yl)diaminostilbene-2,2'-disulfonic Acid Derivatives as Fluorescent Brighteners [II]

  • Jung, Jongkeun;Kang, Yonghan
    • Bulletin of the Korean Chemical Society
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    • v.34 no.7
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    • pp.2131-2137
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    • 2013
  • In this work, the key intermediate, 4-amino-4'-(2-amino-4-anilino-1,3,5-triazine-6-yl)-aminostilbene-2,2'-disulfonic acid, was prepared from 4-(2-amino-4-anilino-1,3,5-triazine-6-yl)amino-4'-nitrostilbene-2,2'-disulfonate by using Tin(II) chloride as the reducing agent. Using this intermediate, nineteen new asymmetrically substituted bistriazinylstilbene fluorescent brightening agents were synthesized. Chemical structures of the obtained compounds 5a-s were analyzed by proton NMR spectrum. The physical properties of the new compounds 5a-s were characterized by fastness test and whiteness measurement test and the obtained data were compared to measurements obtained from CI 86.

Physiological, Pharmacological and Toxicological Implications of Heterodimeric Amino Acid Transporters

  • Kanai, Yoshikatsu;Endou, Hitoshi
    • The Korean Journal of Physiology and Pharmacology
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    • v.8 no.3
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    • pp.117-127
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    • 2004
  • The heterodimeric amino acid transporter family is a subfamily of SLC7 solute transporter family which includes 14-transmembrane cationic amino acid transporters and 12-transmembrane heterodimeric amino acid transporters. The members of heterodimeric amino acid transporter family are linked via a disulfide bond to single membrane spanning glycoproteins such as 4F2hc (4F2 heavy chain) and rBAT $(related\;to\;b^0,\;^+-amino\;acid\;transporter)$. Six members are associated with 4F2hc and one is linked to rBAT. Two additional members were identified as ones associated with unknown heavy chains. The members of heterodimeric amino acid transporter family exhibit diverse substrate selectivity and are expressed in variety of tissues. They play variety of physiological roles including epithelial transport of amino acids as well as the roles to provide cells in general with amino acids for cellular nutrition. The dysfunction or hyperfunction of the members of the heterodimeric amino acid transporter family are involved in some diseases and pathologic conditions. The genetic defects of the renal and intestinal transporters $b^{0,+}AT/BAT1\;(b^{0,+}-type\;amino\;acid\;transporter/b^{0,+}-type\;amino\;acid\;transporter\;1)$ and $y^+LAT1\;(y^+L-type\;amino\;acid\;transporter\;1)$ result in the amino aciduria with sever clinical symptoms such as cystinuria and lysin uric protein intolerance, respectively. LAT1 is proposed to be involved in the progression of malignant tumor. xCT (x-C-type transporter) functions to protect cells against oxidative stress, while its over-function may be damaging neurons leading to the exacerbation of brain damage after brain ischemia. Because of broad substrate selectivity, system L transporters such as LAT1 transport amino acid-related compounds including L-Dopa and function as a drug transporter. System L also interacts with some environmental toxins with amino acid-related structure such as cysteine-conjugated methylmercury. Therefore, these transporter would be candidates for drug targets based on new therapeutic strategies.

Studies on the Synthesis and Antibacterial Activity of 2-Ethoxymethyl-3-(5-nitro-2-furyl)acrylamide Derivatives (2-Ethoxymethyl-3-(5-nitro-2-furyl)acrylamide 유도체(誘導體)의 합성(合成) 및 항균작용(抗菌作用)에 관(關)한 연구(硏究))

  • Ko, Ok-Hyun
    • Journal of Pharmaceutical Investigation
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    • v.10 no.4
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    • pp.8-22
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    • 1980
  • In order obtain some new antibacterial agents, seven new 2-ethoxymethyl-3-(5-nitro-2-furyl) acrylamide derivatives were synthesized by condensing 2-ethoxymethyl-3-(5-nitro-2-furyl) acyloyl chloride with amino compounds namely 5-amino-3, 4-dimethyl isoxazole, sulfamonomethoxazole, d-2-amino-1-butanol, hydroxylamine hydrochloride, semicarbazide hydrochloride, thiosemicarbazide, and p, p'-diaminodiphenylsulfone, respectively. The seven synthesized compounds were 2-ethoxymethyl-3-(5-nitro-2-furyl) acryl-5-amino-3, 4-dimethylisoxazoleamide [VII], $N^4-[2-ethoxymethyl\;3-methyl\;(5-nitro-2-furyl)\;acryl]-N^1-(5-methyl-3-isoxazolyl)$ sulfanilamide [VIII], 2-ethoxyl-3-(5-nitro-2-furyl) acrylsemicarbazide [X], 2-ethoxymethyl-3-(5-nitro-2-furyl) acrylthiosemicarbazide [XI], 2-ethoxymethyl-3-(5-nitro-2-furyl) acryl-d-2-amino-1-butanolamide [XII], and 4, 4'-di[2-ethoxymethyl-3-(5-nitro-2-furyl) acryl-amido] diphenylsulfone [XIII]. These compounds, with exception of the compound XIII, showed generally effective antibacterial activity, especially in the following instances. Compound VII was shown to be effective against Bacillus subtilis ATCC 6633 compound VIII, against Bacillus cereus var. Mycoides ATCC 1778, and compound XII, against both Proteus vuglaris and Saccharomyces cerevisiae ATCC 9763.

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