N5-(氨基硫代甲酰)-N2-[(1,1-二甲基乙氧基)羰基]-L-鸟氨酸叔丁酯 | 133565-49-8

• 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
• 中文名称: N5-(氨基硫代甲酰)-N2-[(1,1-二甲基乙氧基)羰基]-L-鸟氨酸叔丁酯
• 英文名称: α-N-t-butoxycarbonyl-δ-(thioureido)-L-norvaline-t-butyl ester
• 英文别名: tert-butyl (2S)-5-(carbamothioylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 133565-49-8
• 化学式: C₁₅H₂₉N₃O₄S
• 分子量: 347.479
• InChiKey: BZCHKHCGOVKYIY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-L-thiocitrulline-OtBu
tert-butyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-5-(carbamothioylamino)pentanoate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Boc-L-thiocitrulline-OtBu
CAS number: 133565-49-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C15H29N3O4S
Molecular weight: 347.5

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N5-(氨基硫代甲酰)-N2-[(1,1-二甲基乙氧基)羰基]-L-鸟氨酸叔丁酯 在 palladium on activated charcoal 盐酸 、 氢气 、 碳酸氢钠 、 silver nitrate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 乙腈 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 50.5h， 生成 Nw-Hydroxyl-L-arginine Dihydrochloride
  参考文献：
  名称：

  Synthesis of the putative l-arginine metabolite L-NG-hydroxyarginine

  摘要：

  Syntheses of L-N(G)-hydroxyarginine (1), the putative biosynthetic precursor of nitric oxide, and the N-15 labelled analogs 9 and 10 using L-ornithine as the enantiopure starting material is reported.

  DOI：

  10.1016/s0040-4039(00)92109-9
• 作为产物：
  描述：

  α-N-tert-butoxycarbonyl-δ-N-isothiocyanato-L-ornithine tert-butyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N5-(氨基硫代甲酰)-N2-[(1,1-二甲基乙氧基)羰基]-L-鸟氨酸叔丁酯
  参考文献：
  名称：

  Synthesis of the putative l-arginine metabolite L-NG-hydroxyarginine

  摘要：

  Syntheses of L-N(G)-hydroxyarginine (1), the putative biosynthetic precursor of nitric oxide, and the N-15 labelled analogs 9 and 10 using L-ornithine as the enantiopure starting material is reported.

  DOI：

  10.1016/s0040-4039(00)92109-9

文献信息

• Heterocyclic analogues of l -citrulline as inhibitors of the isoforms of nitric oxide synthase (NOS) and identification of N δ -(4,5-dihydrothiazol-2-yl)ornithine as a potent inhibitor
  作者：Saraj Ulhaq、Edwin C Chinje、Matthew A Naylor、Mohammed Jaffar、Ian J Stratford、Michael D Threadgill

  DOI：10.1016/s0968-0896(99)00136-4

  日期：1999.9

  synthesised. In two of these, the S-substituent was 'tied back' sterically by cyclisation to the nitrogen remote from the amino-acid unit. N(delta)-(4,5-Dihydrothiazol-2-yl)ornithine was identified as an inhibitor of rat inducible and constitutive isoforms of NOS and of a constitutive NOS derived from a human tumour xenograft. Analogous N(delta)-(thiazol-2-yl)ornithines were less active, whereas the corresponding

  L-硫代瓜氨酸是已知的几种一氧化氮合酶 (NOS) 同种型的强效抑制剂。为了比以前报道的更深入地探索该分子的构效关系 (SAR)，合成了三种取代异硫脲硫的类似物。在其中两个中，通过环化到远离氨基酸单元的氮，S-取代基被空间“束缚”。N(delta)-(4,5-Dihydrothiazol-2-yl)ornithine 被确定为大鼠诱导型和组成型 NOS 和源自人类肿瘤异种移植物的组成型 NOS 的抑制剂。类似的 N(delta)-(thiazol-2-yl)ornithines 活性较低，而相应的 N(delta)-(oxazol-2-yl)ornithine 和 N(delta)-(pyrimidin-2-yl)ornithine 完全失效抑制 NOS。已开发出一种新的有效制备关键合成中间体 N(α)-Boc-硫代瓜氨酸叔丁酯的方法。用 2-氨基-5-(杂环硫基)戊酸（由 2-(Boc-
• Nª -Hydroxy-L-Arginine Derivatives for the Treatment of Diseases
  申请人：Clement Bernd

  公开号：US20120123111A1

  公开（公告）日：2012-05-17

  The present invention relates to physically-chemically and pharmacokinetically enhanced N ω -hydroxy-L-arginine (NOHA) derivatives and a method for producing the NOHA derivatives having enhanced physical-chemical and pharmacokinetic properties according to the invention.

  本发明涉及一种物理化学和药代动力学增强的Nω-羟基-L-精氨酸（NOHA）衍生物，以及根据本发明制备具有增强物理化学和药代动力学性能的NOHA衍生物的方法。
• Substituted urea and isothiourea derivatives as no synthase inhibitors
  申请人：——

  公开号：US20010034342A1

  公开（公告）日：2001-10-25

  The use of an N-substituted urea derivative for the manufacture of a medicament for the treatment of a condition where there is an advantage in inhibiting the NO synthase enzyme, in particular cerebral ischemia, and pharmaceutical formulations therefor are disclosed. Novel N-substituted urea derivatives and processes for the preparation thereof are also described.

  本发明涉及使用N-取代脲衍生物制备药物，用于治疗需要抑制NO合酶酶的情况，特别是脑缺血，并公开了相应的制剂。同时还描述了新型N-取代脲衍生物及其制备方法。
• Narayanan; Griffith, Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 885 - 887
  作者：Narayanan、Griffith

  DOI：——

  日期：——
• HEME BINDING COMPOUNDS AND USE THEREOF
  申请人：MEDICAL COLLEGE OF WISCONSIN RESEARCH FOUNDATION, INC.

  公开号：EP0707577A1

  公开（公告）日：1996-04-24