N^α-(tert-butyloxycarbonyl)-N^α-methyl-L-ornithine | 161561-60-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N^α-(tert-butyloxycarbonyl)-N^α-methyl-L-ornithine
• 英文别名: Boc-N-Me-Orn；(2S)-5-amino-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid
• CAS: 161561-60-0
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: VKAPLRSMSUCBEO-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-(tert-butyloxycarbonyl)-N^α-methyl-L-ornithine 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2S)-2-(methylamino)-5-(3-nitroguanidino)pentanoic acid piperidin-4-ylamide trifluoroacetic salt
  参考文献：
  名称：

  Selective l-nitroargininylaminopyrrolidine and l-nitroargininylaminopiperidine neuronal nitric oxide synthase inhibitors

  摘要：

  Selective inhibition of the localized excess production of NO by neuronal nitric oxide synthase (nNOS) has been targeted as a potential means of treating various neurological disorders. Based on observations from the X-ray crystal structures of complexes of nNOS with two nNOS-selective inhibitors, (4S)-N-{4-amino-5-[(2-amino)ethylamino]pentyl}-N'-nitroguanidine (L-Arg(NO2)-L-Dbu-NH2 (1) and 4-N-(N-omega-nitro-L-argininyl)-trans-4-amino-L-proline amide (2), a series of descarboxamide analogues was designed and synthesized (3-7). The most potent compound was aminopyrrolidine analogue 3, which exhibited better potency and selectivity for nNOS than parent compound 2. In addition, 3 provided higher lipophilicity and a lower molecular weight than 2, therefore having better physicochemical properties. N-alpha-Methylated analogues (8-11) also were prepared for increased lipophilicity of the inhibitors, but they had 4- to 5-fold weaker binding affinity compared to their parent compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.001
• 作为产物：
  描述：

  Boc-L-谷氨酰胺 在 platinum(IV) oxide 盐酸 、 氢气 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 异丙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 1.0h， 生成 N^α-(tert-butyloxycarbonyl)-N^α-methyl-L-ornithine
  参考文献：
  名称：

  的新颖的合成ñ α -甲基精氨酸和Ñ α -甲基-鸟氨酸衍生物

  摘要：

  Ñ α -Boc- Ñ α甲基Ñ ω，ω ' -双（苄氧羰基） -大号-精氨酸和Ñ α -Boc- Ñ α甲基Ñ δ苄氧基羰基大号鸟氨酸开始的Boc-已经合成L- Gln。将Boc- L -Gln的γ-羧酰胺脱水成腈基，然后将生成的化合物选择性地甲基化，得到N -Boc-2-甲基氨基-4-氰基丁酸。然后将腈还原成胺家具关键中间体Ñ α -Boc-Ñ α甲基大号鸟氨酸。

  DOI：

  10.1016/0040-4039(94)02210-3

文献信息

• Novel synthesis of Nα-methyl-arginine and Nα-methyl-ornithine derivatives
  作者：Chu-Biao Xue、William F. DeGrado

  DOI：10.1016/0040-4039(94)02210-3

  日期：1995.1

  Nα-Boc-Nα-methyl-Nω,ω′-bis(benzyloxycarbonyl)-L-arginine and Nα-Boc-Nα-methyl-Nδ-benzyloxycarbonyl-L-ornithine have been synthesized starting with Boc-L-Gln. The γ-carboxamide of Boc-L-Gln was dehydrated to a nitrile group and the resulting compound is selectively methylated providing N-Boc-2-methylamino-4-cyanobutyric acid. The nitrile is then reduced to an amine furnishing the key intermediate N

  Ñ α -Boc- Ñ α甲基Ñ ω，ω ' -双（苄氧羰基） -大号-精氨酸和Ñ α -Boc- Ñ α甲基Ñ δ苄氧基羰基大号鸟氨酸开始的Boc-已经合成L- Gln。将Boc- L -Gln的γ-羧酰胺脱水成腈基，然后将生成的化合物选择性地甲基化，得到N -Boc-2-甲基氨基-4-氰基丁酸。然后将腈还原成胺家具关键中间体Ñ α -Boc-Ñ α甲基大号鸟氨酸。
• Cyclic peptide derivative
  申请人：——

  公开号：US20030191053A1

  公开（公告）日：2003-10-09

  The present invention aims to provide cyclic peptide derivatives having motilin receptor antagonist activity or the like and useful as pharmaceuticals. The present invention provides a compound of general formula ( 1 ): 1 wherein R 1 represents an optionally substituted phenyl group or the like; R 2 represents an amino group or the like; R 3 to R 6 represent a hydrogen atom, a methyl group or the like; R 7 represents a hydrogen atom or the like; V to Z represent a carbonyl group or a methylene group; m represents an integer of 0-2; and n represents an integer of 0-3; or a hydrate or a pharmaceutically acceptable salt thereof.

  本发明旨在提供具有胃动素受体拮抗活性等的环肽衍生物，可用作药物。本发明提供通式（1）的化合物：其中，R1表示可选取代的苯基或类似物；R2表示氨基或类似物；R3到R6表示氢原子、甲基基团或类似物；R7表示氢原子或类似物；V至Z表示羰基基团或亚甲基基团；m表示0-2的整数；n表示0-3的整数；或其水合物或药学上可接受的盐。
• Cyclic motilin receptor antagonists
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US07018981B2

  公开（公告）日：2006-03-28

  The present invention aims to provide cyclic peptide derivatives having motilin receptor antagonist activity and are useful as pharmaceuticals. The present invention provides compounds of general formula (1): wherein R1 represents an optionally substituted phenyl group or the like; R2 represents an amino group or the like; R3 to R6 represent a hydrogen atom, a methyl group or the like; R7 represents a hydrogen atom or the like; V to Z represent a carbonyl group or a methylene group; m represents an integer of 0–2; and n represents an integer of 0–3; or a hydrate or a pharmaceutically acceptable salt thereof.

  本发明旨在提供具有胃动素受体拮抗活性的环肽衍生物，可用作药物。本发明提供一般式（1）的化合物：其中R1代表可选取代的苯基或类似物；R2代表氨基或类似物；R3到R6代表氢原子，甲基基团或类似物；R7代表氢原子或类似物；V到Z代表羰基基团或亚甲基基团；m表示0-2的整数；n表示0-3的整数；或其水合物或药学上可接受的盐。
• Selective l-nitroargininylaminopyrrolidine and l-nitroargininylaminopiperidine neuronal nitric oxide synthase inhibitors
  作者：Jiwon Seo、Pavel Martásek、Linda J. Roman、Richard B. Silverman

  DOI：10.1016/j.bmc.2007.01.001

  日期：2007.3

  Selective inhibition of the localized excess production of NO by neuronal nitric oxide synthase (nNOS) has been targeted as a potential means of treating various neurological disorders. Based on observations from the X-ray crystal structures of complexes of nNOS with two nNOS-selective inhibitors, (4S)-N-4-amino-5-[(2-amino)ethylamino]pentyl}-N'-nitroguanidine (L-Arg(NO2)-L-Dbu-NH2 (1) and 4-N-(N-omega-nitro-L-argininyl)-trans-4-amino-L-proline amide (2), a series of descarboxamide analogues was designed and synthesized (3-7). The most potent compound was aminopyrrolidine analogue 3, which exhibited better potency and selectivity for nNOS than parent compound 2. In addition, 3 provided higher lipophilicity and a lower molecular weight than 2, therefore having better physicochemical properties. N-alpha-Methylated analogues (8-11) also were prepared for increased lipophilicity of the inhibitors, but they had 4- to 5-fold weaker binding affinity compared to their parent compounds. (c) 2007 Elsevier Ltd. All rights reserved.