L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoic acid | 32447-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoic acid
• 英文别名: 2(S)-2-(benzyloxycarbonylamino)-5-hydroxyvaleric acid；N-Carbobenzoxy-δ-hydroxy-L-α-aminovaleriansaeure；N-Cbz-5-hydroxy-L-norvaline；(2S)-5-hydroxy-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 32447-19-1
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: WVGZTPNRQRMWEM-NSHDSACASA-N

物化性质

• 熔点：
  118-122 °C
• 沸点：
  503.8±50.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoic acid 在 盐酸 、 sodium hydroxide 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 54.5h， 生成 L-2-amino-5-(aminooxy)pentanoic acid dihydrochloride
  参考文献：
  名称：

  Insecticidal properties of some derivatives of L-canavanine

  摘要：

  The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production. The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue.

  DOI：

  10.1021/jf00058a034
• 作为产物：
  描述：

  L-谷氨酸-5-甲酯 在 锂硼氢 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 生成 L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoic acid
  参考文献：
  名称：

  Insecticidal properties of some derivatives of L-canavanine

  摘要：

  The canavanine derivatives D-canavanine and L-homocanavanine as well as the 1-methyl and 1-ethyl esters of L-canavanine were synthesized and evaluated for biological activity in fifth instar larvae of the tobacco hornworm, Manduca sexta [Sphingidae]. While L-homocanavanine did not increase intrinsic toxicity, it was as deleterious as L-canavanine. D-Canavanine was biologically active, as demonstrated by its ability to cause larval edema, but the D-enantiomer had little ability to elicit the larval growth inhibition and pupal deformity which are hallmarks of canavanine toxicosis and was postulated to be linked to aberrant protein production. The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability. Our experiments revealed that these esters are less toxic than canavanine; the ethyl ester disrupted larval growth more than did the methyl analogue.

  DOI：

  10.1021/jf00058a034

文献信息

• Preparation of Amino- and Carboxy-ProtectedL-α-Amino-ω-iodocarboxylic Acids
  作者：Johnny Easmon、Gottfried Heinisch、Wolfgang Holzer、Barbara Matuszczak

  DOI：10.1002/ardp.19953280414

  日期：——

  The synthesis of L‐α‐amino‐ω‐iodobutyric, valeric, and caproic acid esters protected at the amino function by a benzyloxycarbonyl group is reported.

  据报道，L-α-氨基-ω-碘丁酸酯、戊酸酯和己酸酯的合成在氨基官能团处被苄氧羰基保护。
• Process for producing hydroxyamino acid derivative
  申请人：——

  公开号：US20040249205A1

  公开（公告）日：2004-12-09

  Provided is a method of preparing a hydroxyamino acid derivative, particularly in an optically active form thereof with high efficiency. Specifically, provided is a method of preparing hydroxyamino acid derivatives represented by Formula (I) or salts thereof: 1 , characterized in that an amino acid derivative represented by Formula (II): 2 is subjected to a selective reduction reaction of a carboxyl group at a side chain terminus in a solvent, and then, optionally, subjected to an elimination reaction of a protecting group of an amino group or a salt-formation reaction of an amino group or a carboxyl group.

  提供了一种高效制备羟基氨基酸衍生物的方法，特别是制备其光学活性形式。具体地，提供了一种制备由公式(I)表示的羟基氨基酸衍生物或其盐的方法：1，其特征在于，在溶剂中对由公式(II)表示的氨基酸衍生物进行侧链末端羧基的选择性还原反应，然后，可选择进行氨基保护基的消除反应或氨基或羧基的盐形成反应。
• [EN] ANTI-CANCER COMPOUNDS CONTAINING CYCLOPENTAQUINAZOLINE RING<br/>[FR] COMPOSES ANTI-CANCER CONTENANT UN NOYAU DE CYCLOPENTAQUINAZOLINE
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：WO1995030673A1

  公开（公告）日：1995-11-16

  (EN) Cyclopentaquinazoline of formula (I), wherein R1 is hydrogen, amino, C1-4 alkyl, C1-4 alkoxy, C1-4 hydroxyalkyl or C1-4 fluoroalkyl; wherein R2 is hydrogen, C1-4 alkyl, C3-4 alkenyl, C3-4 alkynyl, C2-4 hydroxyalkyl, C2-4 halogenoalkyl or C1-4 cyanoalkyl; Ar1 is phenylene, thiophenediyl, thiazolediyl, pyridinediyl or pyrimidinediyl which may optionally bear one or two substituents selected from halogeno, hydroxy, amino, nitro, cyano, trifluoromethyl, C1-4 alkyl and C1-4 alkoxy; and wherein R3 is a group of the formula: -A1-Ar2-A2-Y1, in which A1 is a bond between the $g(a)-carbon atom of the group -CONHCH(CO2H)- and Ar2 or is a C1-2 alkylene group; Ar2 is phenylene, tetrazoldiyl, tiophenediyl, thiazolediyl, pyridinediyl or pyrimidinediyl which in the case of phenylene may optionally bear one or two substituents on the ring selected from halogeno, nitro, C1-4 alkyl and C1-4 alkoxy; A2 is a C1-3 alkylene or C2-3 alkenylene group; and a pharmaceutically acceptable salt or ester thereof are of therapeutic value particularly in the treatment of cancer.(FR) Cyclopentaquinazoline représenté par la formule (I), dans laquelle R1 représente hydrogène, amino, alkyle C1-4, alcoxy C1-4 , hydroxyalkyle C1-4 ou fluoroalkyle C1-4; dans laquelle R2 représente hydrogène, alkyle C1-4, alcényle C3-4, alcynyle C3-4, hydroxyalkyle C2-4, alogénoalkyle C2-4 ou cyanoalkyle C1-4; Ar1 représente phenylène, thiophénediyle, thiazolediyle, pyridinediyle ou pyrimidinediyle pouvant éventuellement porter un ou deux substituants sélectionés à partir de halogéno, hydroxy, amino, nitro, cyano, trifluorométhyle, alkyle C1-4 et alcoxy C1-4; et dans laquelle R3 représente un groupe de formule: -A1-Ar2-A2-Y1, dans laquelle A1 représente une liaison entre l'atome de $g(a)-carbone du groupe -CONHCH(CO2H) et un groupe alkylène C1-2; Ar2 représente phénylène, tétrazoldiyle, tiophénediyle, thiazolediyle, pyridinediyle ou pyrimidinediyle qui, dans le cas de phénylène, peut éventuellement porter un ou deux substituants sur le noyau sélectionnés à partir de halogéno, nitro, alkyle C1-4 et alcoxy C1-4; A2 représente un groupe alkylène C1-3 ou alkénylène C2-3; ainsi qu'un de ses sels ou de ses esters présentant une valeur thérapeutique, en particulier, dans le traitement du cancer.

  (I)式中的环戊喹唑啉，其中R1为氢、氨基、C1-4烷基、C1-4烷氧基、C1-4羟基烷基或C1-4氟代烷基；R2为氢、C1-4烷基、C3-4烯基、C3-4炔基、C2-4羟基烷基、C2-4卤代烷基或C1-4氰基烷基；Ar1为苯基、噻吩二基、噻唑二基、吡啶二基或嘧啶二基，可选地带有一个或两个卤代、羟基、氨基、硝基、氰基、三氟甲基、C1-4烷基和C1-4烷氧基取代基；R3为以下公式的基团：-A1-Ar2-A2-Y1，其中A1为连接基团-CONHCH（CO2H）的$g(a)-碳原子和Ar2之间的键或C1-2烷基链；Ar2为苯基、四唑二基、噻吩二基、噻唑二基、吡啶二基或嘧啶二基，若为苯基，则可选地在环上带有一个或两个卤代、硝基、C1-4烷基和C1-4烷氧基取代基；A2为C1-3烷基链或C2-3烯基链；以及其药学上可接受的盐或酯，特别是在癌症治疗方面具有治疗价值。
• SULFONYLAMINOVALEROLACTAMS AND DERIVATIVES THEREOF AS FACTOR XA INHIBITORS
  申请人：Han Wei

  公开号：US20070099922A1

  公开（公告）日：2007-05-03

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula Ia-If: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了式Ia-If的磺酰氨基戊内酰内酰胺及其衍生物或其药学上可接受的盐形式，其中环G是单环或双环碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是Xa因子的抑制剂。
• Lactol derivatives as inhibiters of cathepsin L
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0641800A1

  公开（公告）日：1995-03-08

  The present invention provides novel compound of the formulas (Ia) or (I): wherein Q is one or two amino acid residues which may be substituted; R³ is a carboxyl group which may be esterified or an acyl group; A is an alkylene group; B is hydrogen or an alkyl group which may be substituted or an acyl group; or a salt thereof; wherein R¹ and R² may be the same or different and each is hydrogen or a hydrocarbon residue which may be substituted; R³, A and B have the same definitions as those shown above; m and n each is 0 or 1; provided that where both m and n are both equal to 0, R³ is a carboxyl group which may be esterified or an acyl group having not less than 7 carbon atoms; or a salt thereof. The compound (Ia) or (I) shows cathepsin L inhibitory and bone resorption inhibitory activities and are useful as a prophylactic/therapeutic agent for osteoporosis.

  本发明提供了式 (Ia) 或 (I) 的新型化合物： 其中 Q 是一个或两个可被取代的氨基酸残基；R³ 是可被酯化的羧基或酰基；A 是亚烷基；B 是氢或可被取代的烷基或酰基；或其盐； 其中R¹和R²可以相同或不同，且各自为氢或可被取代的烃残基；R³、A和B的定义与上表所示相同；m和n各自为0或1；但当m和n均等于0时，R³为可酯化的羧基或具有不少于7个碳原子的酰基；或其盐。 化合物（Ia）或（I）具有抑制 cathepsin L 和抑制骨吸收的活性，可用作骨质疏松症的预防/治疗剂。