1-Amino-3--2-propanol | 63062-22-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Amino-3--2-propanol
• 英文别名: 3-(N-Methyl-N-phenylamino)-2-hydroxypropylamine；N1-methyl-N1-phenyl-1,3-diaminopropan-2-ol；1-amino-3-(N-methyl-anilino)-propan-2-ol；β-Amino-β'-methylanilino-isopropylalkohol；β-Oxy-γ-methylanilino-propylamin；1-Amino-3-[methyl(phenyl)amino]propan-2-ol；1-amino-3-(N-methylanilino)propan-2-ol
• CAS: 63062-22-6
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: HAJBMSKVWATVDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Amino-3--2-propanol 在 镍 磷酸 、 氢气 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 62.5h， 生成 ethyl 5-amino-1,2-dihydro-3-<(N-methyl-N-phenylamino)methyl>pyrido<3,4-b>pyrazine-7-carbamate
  参考文献：
  名称：

  New anticancer agents: synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines)

  摘要：

  Reaction of alpha-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-[(2-oxo-2-phenylethyl)amino]pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4). Related pyridines substituted with a keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4- [[3-(N-methyl-N-phenylamino)-2-hydroxypropyl]amino]-5-nitropyridine-7- carbamates (6). Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7). Several of the oximes 3 were successfully hydrogenated to give 7 directly. The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice. These biological activities are attributed to the accumulation of cells at mitosis.

  DOI：

  10.1021/jm00351a008
• 作为产物：
  描述：

  N-甲基-N-(环氧乙烷-2-基甲基)苯胺 在 氨 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-Amino-3--2-propanol
  参考文献：
  名称：

  New anticancer agents: synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines)

  摘要：

  Reaction of alpha-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-[(2-oxo-2-phenylethyl)amino]pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4). Related pyridines substituted with a keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4- [[3-(N-methyl-N-phenylamino)-2-hydroxypropyl]amino]-5-nitropyridine-7- carbamates (6). Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7). Several of the oximes 3 were successfully hydrogenated to give 7 directly. The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice. These biological activities are attributed to the accumulation of cells at mitosis.

  DOI：

  10.1021/jm00351a008

文献信息

• Thiazolidine and oxazolidine derivatives, their preparation and their
  申请人：Sankyo Company, Limited

  公开号：US05578620A1

  公开（公告）日：1996-11-26

  Compounds of formula (I): ##STR1## and salts, esters and solyates thereof and pro-drugs therefor are useful for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, glucose tolerance insufficiency, insulin resistance and diabetic complications.

  公式（I）的化合物：##STR1##及其盐、酯和溶剂化合物以及其前体药物对于治疗和/或预防多种疾病非常有用，包括但不限于：高脂血症、高血糖、肥胖、葡萄糖耐量不足、胰岛素抵抗和糖尿病并发症。
• Thiazolidine and oxazolidine derivatives their preparation and their
  申请人：Sankyo Company, Limited

  公开号：US05688823A1

  公开（公告）日：1997-11-18

  Compounds of formula (I): ##STR1## Z is a group of formula (iii), (iv),: ##STR2## and salts, esters and solvates thereof and pro-drugs therefor are useful for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, glucose tolerance insufficiency, insulin resistance and diabetic complications.

  公式(I)的化合物：##STR1## 其中，Z是公式(iii)，(iv)的基团：##STR2## 它们的盐、酯和溶剂合物以及其前药可用于治疗和/或预防多种疾病，包括但不限于：高脂血症、高血糖症、肥胖症、葡萄糖耐量不足、胰岛素抵抗和糖尿病并发症。
• Novel 1,2-dihydropyrido-(3,4-b)pyrazines
  申请人：Southern Research Institute

  公开号：EP0090681A2

  公开（公告）日：1983-10-05

  1,2-Dihydropyrido[3,4-b]pyrazines are provided which possess anticancer activity. The compounds have the structure: wherein x has a value of 1, 2 or 3; Y is CH2 or N(CH3); R1is a lower alkyl group; e.g., an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc.; R2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, preferably from about one to about 6 carbon atoms; alkenyl radicals having from about two to about 15 carbon atoms, preferably from about two to about 10 carbon atoms; cycloalkyl radi- cads having from about three to about 20 carbon atoms, preferably from about three to about 15 carbon atoms; aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 15 carbon atoms; a halogen radical, e.g., chlorine, fluorine, bromine and iodine; a hydroxyl group; an amino group; an alkoxy or aryloxy group; an alkylthio group or an arylthio group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl; amino, alkoxy or aryloxy; and, when taken together with the aromatic ring to which it is attached , a fused ring structure such as naphthyl; and R3 and R4 are either both hydrogen or one is hydrogen and the other is a lower alkyl group; provided that when each of R2, R3 and R4 are hydrogen, Y is CH2.

  本研究提供了具有抗癌活性的 1,2-二氢吡啶并[3,4-b]吡嗪类化合物。这些化合物具有如下结构 其中 x 的值为 1、2 或 3；Y 为 CH2 或 N(CH3)；R1 为低级烷基；例如R1 是低级烷基；例如，含有多达六个碳原子的烷基，如甲基、乙基、丙基、丁基等； R2 是选自下列化合物的成员R2 是选自以下组别的成员：氢、具有约 1 至约 12 个碳原子，最好是约 1 至约 6 个碳原子的烷基；具有约 2 至约 15 个碳原子，最好是约 2 至约 10 个碳原子的烯基；具有约 3 至约 20 个碳原子，最好是约 3 至约 15 个碳原子的环烷基；具有约 6 至约 20 个碳原子，最好是约 6 至约 15 个碳原子的芳烷基和烷芳基；卤素基，例如：氯、氟、溴、烷基、烯烷基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、羟基；氨基；烷氧基或芳氧基；烷硫基或芳硫基，具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子；磺酸基或烷基或芳基磺酰基，具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子；烷基或芳基亚磺酰基，具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子；具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子的烷基或芳基一元或二元基团； 如上定义的烃基，带有卤素、羟基、氨基、烷氧基或芳氧基；当与所连接的芳环一起时，为融合环结构，如萘基；以及 R3 和 R4 要么都是氢，要么一个是氢，另一个是低级烷基；条件是当 R2、R3 和 R4 都是氢时，Y 为 CH2。
• 1,7-anellierte 1H-Indol-2-carbonsäure-N-(1,4-benzodiazepin-3-yl)amide
  申请人：Kali-Chemie Pharma GmbH

  公开号：EP0387618A1

  公开（公告）日：1990-09-19

  Es werden Verbindungen der allgemeinen Formel I beschrieben, worin R¹ Wasserstoff, niederes Alkyl oder Cycloalkylalkyl mit 4-7 Kohlenstoffatomen bedeutet, R² Wasserstoff, Halogen, niederes Alkyl, niederes Alkoxy oder Trifluormethyl bedeutet und R³ Wasserstoff, Halogen, niederes Alkyl oder niederes Alkoxy bedeutet oder R² und R³ gemeinsam eine Alkylendioxygruppe bedeuten, R⁴ Cycloalkyl mit 5 bis 6 Kohlenstoffatomen, Thiophen oder gegebenenfalls substituiertes Phenyl bedeutet, R⁵ Wasserstoff oder Halogen bedeutet, R⁶ Wasserstoff, Halogen, niederes Alkyl, niederes Alkoxy oder Trifluormethyl bedeutet und Z für eine Alkylenkette mit 2-4 Kohlenstoffatomen, welche gegebenenfalls durch niederes Alkyl mono-oder disubstituiert sein kann oder an welche gegebenenfalls ein 5-6-gliedriger carbocyclischer Ring anelliert sein kann, oder für eine -X-CH₂-CH₂-kette steht. Die Verbindungen besitzen pharmakologisch wertvolle Eigen­schaften.

  所述化合物的通式为 I 其中 R¹ 是氢、低级烷基或具有 4-7 个碳原子的环烷基烷基、 R² 是氢、卤素、低级烷基、低级烷氧基或三氟甲基，以及 R³ 表示氢、卤素、低级烷基或低级烷氧基，或 R² 和 R³ 共同表示烷二氧基、 R⁴ 表示具有 5-6 个碳原子的环烷基、噻吩或任选取代的苯基、 R⁵ 表示氢或卤素、 R⁶ 表示氢、卤素、低级烷基、低级烷氧基或三氟甲基，以及 Z 是含有 2-4 个碳原子的亚烷基链、 Z 是具有 2-4 个碳原子的亚烷基链，可选择由低级烷基单取代或二取代，或可选择与 5-6 元碳环融合，或代表-X-CH₂-CH₂链。 这些化合物具有宝贵的药理特性。
• Thiazolidine and oxazolidine derivatives, their preparation and their medical use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0678511A2

  公开（公告）日：1995-10-25

  Compounds of formula (I) : [in which : R1 and R2 are each hydrogen or alkyl, or together a group of formula -(CH2)k- in which k is an integer ; R3 is hydrogen, alkyl, alkoxy, halogen or hydroxy ; A and B are each hydrogen, alkyl, aralkyl, aliphatic carboxylic acyl, aryl-substituted aliphatic carboxylic acyl, aromatic carboxylic acyl or carbamoyl, or A and B together represent >C=O, >C=S, -C(=O)-C(=O)-, -CH2C(=0)-, -CH2CH2-, -SO2- or -CH2SO2- ; X is a group of formula : W-(CH2)m-X1- in which W is aryl or heterocyclic, X1 is a single bond, oxygen, sulphur or >NR4 in which R4 is hydrogen, alkyl, aralkyl or aryl, and m is 0 or an integer ; Y is a group of formula : -(CH2)n-Y1-, in which Y1 is a single bond, oxygen or sulphur, and n is an integer ; Z is a group of formula (i), (ii), (iii), (iv), (v) or (vi) : in which R5 is hydrogen, carboxyalkyl, alkanoyloxyalkyl, cycloalkyl-substituted alkanoyloxyalkyl, cycloalkylcarbonyloxyalkyl, alkoxycarbonyloxyalkyl, cycloalkyl-substituted alkoxycarbonyloxyalkyl or cycloalkyloxycarbonyloxyalkyl group] ; and salts, esters and solvates thereof and pro-drugs therefor are useful for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, glucose tolerance insufficiency, insulin resistance and diabetic complications.

  式(I)化合物： [其中 ：R1 和 R2 分别为氢或烷基，或共同为式-(CH2)k-的基团，其中 k 为整数；R3 为氢、烷基、烷氧基、卤素或羟基；A 和 B 分别是氢、烷基、芳烷基、脂肪族羧酰基、芳基取代的脂肪族羧酰基、芳香族羧酰基或氨基甲酰基，或者 A 和 B 共同代表 >C=O、>C=S、-C(=O)-C(=O)-、-CH2C(=0)-、-CH2CH2-、-SO2- 或 -CH2SO2-；X 是一个式基团：W-(CH2)m-X1-，其中 W 是芳基或杂环，X1 是单键、氧、硫或 >NR4，其中 R4 是氢、烷基、芳基或芳基，m 是 0 或整数； Y 是式中的基团 ：-(CH2)n-Y1-，其中 Y1 是单键、氧或硫，n 是整数； Z 是式(i)、(ii)、(iii)、(iv)、(v)或(vi)的基团： 其中 R5 是氢、羧基烷基、烷酰氧基烷基、环烷基取代的烷酰氧基烷基、环烷基羰基氧基烷基、烷氧基羰基氧基烷基、环烷基取代的烷氧基羰基氧基烷基或环烷氧基羰基氧基烷基]；其盐类、酯类和溶解物及其原药可用于治疗和/或预防多种疾病，包括以下一种或多种疾病：高脂血症、高血糖、肥胖、葡萄糖耐量不足、胰岛素抵抗和糖尿病并发症。