5-aminooxypentanoic acid hydrochloride | 15985-56-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-aminooxypentanoic acid hydrochloride
• 英文别名: 5-(Aminooxy)pentanoic acid hydrochloride；5-aminooxypentanoic acid;hydrochloride
• CAS: 15985-56-5
• 化学式: C₅H₁₁NO₃*ClH
• 分子量: 169.608
• InChiKey: SEYWVXSUGOEOAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-aminooxypentanoic acid hydrochloride 在 吡啶 、 盐酸 作用下， 生成 5-[(R)-2-Hydroxy-1,3-diphenyl-prop-(E)-ylideneaminooxy]-pentanoic acid ethyl ester
  参考文献：
  名称：

  Nucleophilic substitution on α-mesyloxy-O-alkyloximes—I. Enantiospecific synthesis of 2-(imidazol-1-yl)-1,3-diphenylpropan-1-one O-alkyloximes

  摘要：

  An enantiospecific synthesis of (S)- and (R)-(E)-5-[1,3-diphenyl-2-(imidazol-l-yl)propylidene] aminooxypentanoic acids 1 using homochiral phenylalanines as starting material is described. Chiral alpha-hydroxyketones 9 were obtained from alpha-hydroxyacids 7 by Weinreb's ketone synthesis. Imidazole introduction by nucleophilic substitution on mesylate 10 led to 2-(imidazol-1-yl)propan-1-one derivative 3, key intermediate in the synthesis of 1. However, the low configurational stability displayed by compound 3 compromised its use in an enantiospecific synthesis. Homochiral compounds 1 were then obtained by a nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes 14 which were in turn obtained from 9. This nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes was not previously reported either on homochiral compounds or on racemic derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00505-8

文献信息

• Agents Combining Thromboxane Receptor Antagonism with Thromboxane Synthase Inhibition: [[[2-(1H-Imidazol-1-yl)ethylidene]amino]oxy]alkanoic Acids
  作者：Paolo Cozzi、Antonio Giordani、Maria Menichincheri、Antonio Pillan、Vittorio Pinciroli、Arsenia Rossi、Roberto Tonani、Daniele Volpi、Monica Tamburin

  DOI：10.1021/jm00047a016

  日期：1994.10

  A new class of compounds combining thromboxane-A2 (TxA2) receptor antagonism and thromboxane synthase inhibition is described. A first series of (E)- and (Z)-[[[2-(1H-imidazol-1-yl)ethylidene]amino]oxy]pentanoic acids showed relevant thromboxane synthase inhibition associated with weak TxA2 receptor antagonism, while a series of (+/-)-(E)-[[[2-(1H-imidazol-1-yl)-3-phenylpropylidene]amino]oxy] pentanoic

  描述了结合血栓烷-A2（TxA2）受体拮抗作用和血栓烷合酶抑制作用的一类新化合物。第一个系列（E）-和（Z）-[[[[2-（1H-咪唑-1-基）亚乙基]氨基]氧基]戊酸显示相关的血栓烷合酶抑制与弱TxA2受体拮抗作用有关，而一系列前者在结构上衍生自（+/-）-（E）-[[[[2-（1H-咪唑-1-基）-3-苯基亚丙基]氨基]氧基]戊酸的戊酸显示有效且均衡的双重活动。讨论了重要的单一活动和双重活动的结构要求。后一个系列的两个紧密同源物，（+/-）-（E）-5-[[[[1-环己基-2-（1H-咪唑-1-基）-3-苯基亚丙基]氨基]氧基]戊酸23c及其对氟苯基类似物23m在凝结期间抑制大鼠全血中TxB2的产生，IC50为0.06和0。37 microM拮抗[3H] SQ 29548与洗涤的人血小板的结合，IC50分别为0.08和0.02 microM。选择这两种化合物进行进一步的药理评估，结果显
• 2-(Imidazol-1-yl)-3-heteroarylpropylidene-aminoxyalkanoic acid derivatives
  申请人：PHARMACIA S.p.A.

  公开号：EP0611765A1

  公开（公告）日：1994-08-24

  The invention relates to compounds of formula (I) wherein A is a heteromonocyclic ring selected from furanyl, pirazinyl, pyrimidyl and pyridazinyl which may be unsubstituted or substituted by a substituent chosen from halogen, C₁-C₄ alkyl and CF₃; R₁ is a) phenyl unsubstituted or substituted by halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy or CF₃; b) cyclohexyl; or c) a straight or branched C₁-C₆ alkyl group; T is a branched or straight C₃-C₅ alkylene chain; R₂ is hydrogen or C₁-C₄ alkyl, and the pharmaceutically acceptable salt thereof, which are useful as selective inhibitors of thromboxane A₂ (TxA₂) synthesis and TxA₂ antagonists.

  本发明涉及式（I）的化合物，其中A是从呋喃基，吡嗪基，嘧啶基和吡嗪嗪基中选择的杂环单环，可以是未取代或取代的，所述取代基被选择为卤素，C₁-C₄烷基和CF₃; R₁是a）苯基未取代或取代的卤素，C₁-C₄烷基，C₁-C₄烷氧基或CF₃; b）环己基; 或c）直链或支链C₁-C₆烷基; T是支链或直链C₃-C₅烷基链; R₂是氢或C₁-C₄烷基，以及其药学上可接受的盐，其作为选择性血栓素A₂（TxA₂）合成抑制剂和TxA₂拮抗剂有用。
• 2-(Imidazol-1-yl)2-benzylethylidene-aminooxyalkyl-hydroxamic acid derivatives
  申请人：PHARMACIA S.p.A.

  公开号：EP0635494A1

  公开（公告）日：1995-01-25

  A compound having the formula (I) wherein Ais a phenyl ring unsubstituted or substituted by one to three substituents independently chosen from halogen, CF₃, C₁-C₄ alkyl and C₁-C₄ alkoxy; R₁is phenyl unsubstituted or substituted by halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy or CF₃; C₅-C₆ cycloalkyl; or a straight or branched C₁-C₆ alkyl group; Tis a branched or straight C₃-C₅ alkylene chain; Wis a group -OR or in which R is hydrogen or C₁-C₄ alkyl; or a pharmaceutically acceptable salt thereof; and wherein when, at the same time A is a phenyl ring unsubstituted or substituted either by C₁-C₄ alkoxy or by one or two substituents chosen from halogen and CF₃ and R₁ is a phenyl ring unsubstituted or substituted by halogen, CF₃ or C₁-C₄ alkoxy; C₅-C₆ cycloalkyl; or C₁-C₆ alkyl, then W is other than a group -OR as defined above, which is useful as inhibitor of thromboxane A₂ (TxA₂) synthesis.

  化合物的化学式为（I），其中A是苯环，未取代或被一个到三个取代基取代，这些取代基独立地选择自卤素、CF₃、C₁-C₄烷基和C₁-C₄烷氧基；R₁是苯环，未取代或被卤素、C₁-C₄烷基、C₁-C₄烷氧基或CF₃取代；C₅-C₆环烷基；或是直链或支链的C₁-C₆烷基；T是支链或直链的C₃-C₅烷基链；W是-OR基团，其中R是氢或C₁-C₄烷基；或其药学上可接受的盐；当A同时是未取代或被C₁-C₄烷氧基或由卤素和CF₃中选择的一个或两个取代基取代的苯环，且R₁是未取代或被卤素、CF₃或C₁-C₄烷氧基取代的苯环、C₅-C₆环烷基或C₁-C₆烷基时，则W不是上述定义的-OR基团，该化合物可用作凝血素A₂（TxA₂）合成的抑制剂。
• Novel (3.2.0.) bicycloheptanone oxime ethers with valuable therapeutic properties
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0100900A1

  公开（公告）日：1984-02-22

  Compounds useful in treating cardiovascular disorders are the carboxylic acids depicted in formulas (1) and (2) as well as their pharmaceutically acceptable, non-toxic salts and esters, wherein: n is an integer from one to four; R1 is hydroxy; R2 is hydrogen; or R1 and Rz together are an oxo group; R3 is wherein A is -CH2-CH2-; trans-CH=CH-; -C≡C-; and R4 is linear or branched alkyl of one to twelve carbons, cycloalkyl of three to eight carbons; phenyl optionally substituted with one or two identical substituents selected from the group consisting of lower alkyl, lower alkoxy, hydroxy, trifluoromethyl, and halo; or optionally substituted phenylalkyl.

  用于治疗心血管疾病的化合物是式(1)和(2)所示的羧酸类化合物 及其药学上可接受的无毒盐类和酯类，其中 n 是一至四的整数； R1 是羟基 R2 是氢；或 R1 和 Rz 合在一起是一个氧代基团； R3 是 其中 A 是-CH2-CH2-；反式-CH=CH-；-C≡C-；和 R4 是 1 至 12 个碳原子的直链或支链烷基、3 至 8 个碳原子的环烷基、任选被选自低 级烷基、低级烷氧基、羟基、三氟甲基和卤基的一个或两个相同取代基取代的苯基、 或任选被取代的苯基烷基。
• N-imidazolyl derivatives of substituted alkoxyimino tetrahydronaphthalenes and chromans
  申请人：PHARMACIA S.p.A.

  公开号：EP0499444A1

  公开（公告）日：1992-08-19

  The invention provides new imidazole containing alkoxyimino derivatives of tetrahydronaphthalene and chroman of general formula (I) wherein    Z is -CH₂-or-O-;    m is an integer of 1 to 4;    n is zero or 1;    T is a straight or branched, saturated or unsaturatrd C₁-C₆ hydrocarbon chain, or a phenylene radical;    A is a bond or a divalent group consisting of-Si(R′R˝)-; -O-CH₂-,-CF₃-,C(R′R˝)-,vinylene or isopropenylene, wherein each of R′ and R˝being the same or different is hydrogen or C₁-C₄ alkyl;    R is hydrogen or C₁-C₄ alkyl;    R₁ and R₂, being the same, are hydrogen or methyl, or one of R₁ and R₂ is hydrogen and the other is a) a C₁-C₈ alkyl group; b) a C₅-C₈ cycloalkyl or C₅-C₈ cycloalkyl-C₁-C₄ alkyl group, wherein the cycloalkyl group or moiety is unsubstituted or substituted by 1 to 4 C₁-C₄ alkyl groups; or c) an aryl or aryl-C₁-C₄ alkyl group, wherein the aryl group or the aryl moiety is unsubstituted or substituted by 1 to 4 substituents independently chosen from halogen, hydroxy, C₁-C₄ alkyl, trihalo-C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio and C₁-C₄ alkylsulfonyl;    R₃ is hydrogen or a substituent chosen from halogen, hydroxy, C₁-C₄ alkyl, trihalo-C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio and C₁-C₄ alkylsulfonyl;    R₄ is an -OR₅, or -N(R₅ R₆)group, wherein each of R₅ and R₆ independently is hydrogen, C₁-C₆ alkyl, phenyl or benzyl;    and the pharmaceutically acceptable salts thereof, which are useful in the treatment of a disease state in which an anhancement of TxA₂ synthesis exerts a pathogenic effect.

  本发明提供了通式(I)为四氢萘和铬烷的含烷氧基亚氨基的新咪唑衍生物 其中 Z 是-CH₂-或-O-； m 是 1 至 4 的整数 n 为 0 或 1； T 是直链或支链、饱和或不饱和 C₁-C₆烃链，或亚苯基； A 是键或由下列组成的二价基团：-Si(R′R˝)-；-O-CH₂-、-CF₃-、C(R′R˝)-、乙烯基或异亚丙烯基，其中 R′和 R˝ 不论相同或不同均为氢或 C₁-C₄ 烷基； R 是氢或 C₁-C₄ 烷基； R₁和R₂若相同，则为氢或甲基，或R₁和R₂中的一个为氢，另一个为 a) C₁-C₈ 烷基； b) C₅-C₈ 环烷基或 C₅-C₈ 环烷基-C₁-C₄ 烷基，其中环烷基或分子未被取代或被 1 至 4 个 C₁-C₄ 烷基取代；或 c) 芳基或芳基-C₁-C₄烷基，其中芳基或芳基分子未被取代或被 1 至 4 个独立选自卤素的取代基取代、羟基、C₁-C₄ 烷基、三卤代-C₁-C₄ 烷基、C₁-C₄ 烷氧基、C₁-C₄ 烷硫基和 C₁-C₄ 烷磺酰基； R₃ 是氢或选自卤素、羟基、C₁-C₄ 烷基、三卤代-C₁-C₄ 烷基、C₁-C₄ 烷氧基、C₁-C₄ 烷硫基和 C₁-C₄ 烷磺酰基的取代基； R₄ 是 -OR₅，或 -N(R₅ R₆)基团，其中 R₅ 和 R₆ 各自独立地是氢、C₁-C₆ 烷基、苯基或苄基； 及其药学上可接受的盐类，可用于治疗 TxA₂合成增强产生致病作用的疾病。