N-(4-氨基苯(甲)酰)-L-谷氨酸二乙酯 | 13726-52-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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: N-(4-氨基苯(甲)酰)-L-谷氨酸二乙酯
• 中文别名: N-(4-氨基苄酰基)-L-谷氨酸二乙酯；N-(4-氨基苯甲酰基)-L-谷氨酸二乙酯
• 英文名称: diethyl N-(p-aminobenzoyl)-L-glutamate
• 英文别名: N-(4-aminobenzoyl)-L-glutamic acid diethyl ester；Diethyl N-(4-aminobenzoyl)-L-glutamate；diethyl (2S)-2-[(4-aminobenzoyl)amino]pentanedioate
• CAS: 13726-52-8
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: RJXFBLRRPYBPTM-ZDUSSCGKSA-N

物化性质

• 熔点：
  139-142 °C(lit.)
• 沸点：
  460.98°C (rough estimate)
• 密度：
  1.1446 (rough estimate)
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090
• 储存条件：
  常温下应存放在密闭容器中，并置于阴凉、通风和干燥处。

SDS

Name:	N-(P-Aminobenzoyl)-L-Glutamic Acid Diethyl Ester 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	13726-52-8

Section 1 - Chemical Product MSDS Name:N-(P-Aminobenzoyl)-L-Glutamic Acid Diethyl Ester 99% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13726-52-8	N-(P-Aminobenzoyl)-L-Glutamic Acid Die	99%	237-293-1

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13726-52-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 139.00 - 142.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: solubility 2% in ethanol:clear, faint ye
Specific Gravity/Density:
Molecular Formula: C16H22N2O5
Molecular Weight: 322.35

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13726-52-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-(P-Aminobenzoyl)-L-Glutamic Acid Diethyl Ester - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 13726-52-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13726-52-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13726-52-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N-(4-氨基苯甲酰)-L-谷氨酸二乙酯是一种谷氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  N-(4-氨基苯(甲)酰)-L-谷氨酸二乙酯 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 21.0h， 生成 diethyl N-<4--N-(cyanomethyl)amino>benzoyl>-L-glutamate
  参考文献：
  名称：

  叶酸类似物。21.N10-（氰甲基）-5,8-二氮杂萘甲酸的合成及其抗叶酸和抗肿瘤活性。

  摘要：

  通过用氰基甲基取代2的炔丙基部分，合成了抗白血病药物5,8-二氮杂-N10炔丙基叶酸的紧密类似物。该化合物N10-（氰甲基）-5,8-二氮杂萘甲酸（3）在几种生物学测试系统中均经过了抗叶酸和抗肿瘤活性的评估。N-（4-氨基苯甲酰基）-L-谷氨酸二乙酯与溴乙腈的烷基化反应得到N- [4-[（氰基甲基）氨基]苯甲酰基] -L-谷氨酸二乙酯（7）。7与2个氨基6-（溴甲基）-4-羟基喹唑啉（9）在二甲基乙酰胺中的反应生成相应的二乙酯11，将其水解为目标化合物3。还通过使用合成了已知的抗白血病药物2进行比较研究。经过改进的程序，可以提高该产品的产量。通过使用两种需要叶酸的微生物粪便链球菌和干酪乳杆菌，对化合物2和3的抗叶酸活性进行了评估。通过使用培养物中选择的肿瘤细胞，进一步评估了它们作为源自上述生物的胸苷酸合酶和二氢叶酸还原酶的抑制剂，以及它们的抗肿瘤活性。发现化合物2与粪便中的甲氨蝶呤（MTX

  DOI：

  10.1021/jm00358a030
• 作为产物：
  描述：

  N-(4-硝基苯甲酰)-L-谷氨酸二乙酯 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以86%的产率得到N-(4-氨基苯(甲)酰)-L-谷氨酸二乙酯
  参考文献：
  名称：

  室温下水中可持续/可回收的Fe / ppm Pd纳米颗粒催化的安全和选择性硝基还原

  摘要：

  由于无配体的Fe / ppm Pd纳米颗粒与含PEG的设计剂表面活性剂之间具有独特的协同作用，因此在室温下水中存在NaBH 4的情况下，可以轻松，选择性地还原含硝基的芳族化合物和杂芳族化合物。这项新的纳米技术涉及低催化剂负载量，高度化学选择性，并能耐受多种官能团。该过程包括整个水性介质的循环利用，它为减少有价值的含硝基化合物提供了一种通用的，对环境负责的，尤其是安全的方法。

  DOI：

  10.1002/anie.201604026
• 作为试剂：
  描述：

  ethyl 2,2-dimethylthiazolidine-5-carboxylate 在 3 A molecular sieve 、 N-(4-氨基苯(甲)酰)-L-谷氨酸二乙酯 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 22.0h， 生成 benzyl 5-hydroxymethyl-2,2-dimethylthiazolidine-N-carboxylate
  参考文献：
  名称：

  Totani, Reiko; Sako, Magoichi; Hirota, Kosaku, Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 833 - 836

  摘要：

  DOI：

文献信息

• Glutamate aggrecanase inhibitors
  申请人：Sum Phaik-Eng

  公开号：US20070043066A1

  公开（公告）日：2007-02-22

  The present invention relates to modulators of metalloproteinase activity.

  本发明涉及金属蛋白酶活性调节剂。
• Pharmaceutical compounds
  申请人：Burroughs Wellcome Co.

  公开号：US05405851A1

  公开（公告）日：1995-04-11

  The present invention relates to novel benzoquinazoline thymidylate synthase inhibitors, to pharmaceutical formulations containing them and to their use in medicine.

  本发明涉及新型苯并喹唑嘧啶酸甲脱氧胸苷合成酶抑制剂，以及含有它们的药物配方和它们在医学上的应用。
• Anti-tumour agents
  申请人：Imperial Chemical Industries PLC

  公开号：US04992550A1

  公开（公告）日：1991-02-12

  A quinazoline of the formula: ##STR1## wherein R.sup.1 is alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, aryl, aryloxy, arylalkyl, halogeno, hydroxy, mercapto, pyridylthio, pyrimidinylthio, or substituted alkyl or alkoxy; wherein R.sup.2 is hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl or alkanoyl; wherein Ar is phenylene, naphthylene or heterocyclene which is unsubstituted or bears one or more substituents and wherein R.sup.3 is such that R.sup.3 --NH.sub.2 is an amino acid; or a pharmaceutically-acceptable salt or ester thereof. The compounds possess anti-tumour activity.

  一种化学式为：##STR1## 的喹唑啉，其中 R.sup.1 是烷基，环烷基，烯基，炔基，烷氧基，硫代烷基，芳基，芳氧基，芳基烷基，卤素，羟基，巯基，吡啶硫代基，嘧啶硫代基，或取代的烷基或烷氧基；其中 R.sup.2 是氢，烷基，烯基，炔基，取代的烷基或烷酰基；其中 Ar 是苯基，萘基或杂环烯基，未取代或带有一个或多个取代基，且 R.sup.3 是使得 R.sup.3 --NH.sub.2 为氨基酸的基团；或其药用可接受的盐或酯。这些化合物具有抗肿瘤活性。
• Palladium-Catalyzed Silane/Siloxane Reductions in the One-Pot Conversion of Nitro Compounds into Their Amines, Hydroxylamines, Amides, Sulfon­amides, and Carbamates
  作者：Robert Maleczka、Ronald Rahaim

  DOI：10.1055/s-2006-950231

  日期：——

  A combination of palladium(II) acetate, aqueous potassi- um fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their

  醋酸钯 (II)、氟化钾水溶液和聚甲基氢硅氧烷 (PMHS) 的组合有助于在室温下将芳香族硝基化合物还原为苯胺。这些反应往往快速（30 分钟）、高产，并且可以耐受一系列其他官能团。用三乙基硅烷代替 PMHS/KF 可以将脂肪族硝基化合物还原为相应的羟胺。根据底物的不同，这两种条件都可以将产物胺原位转化为酰胺、磺酰胺和氨基甲酸酯。
• Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C-2 position
  作者：Leslie R. Hughes、Ann L. Jackman、John Oldfield、Rodney C. Smith、Kenneth D. Burrows、Peter R. Marsham、Joel A. M. Bishop、Terence R. Jones、Brigid M. O'Connor、A. Hilary Calvert

  DOI：10.1021/jm00173a024

  日期：1990.11

  thymidylate synthase (TS) inhibitor N-[4-[N-[(2-amino-3,4-dihydro-4-oxo-6-quinazolinyl)methyl]-N-prop-2- ynylamino]benzoyl]-L-glutamic acid (1a) has led to the synthesis of quinazoline antifolates bearing alkyl, substituted alkyl, and aryl substituents at C2. In general the synthetic route involved the coupling of the appropriate diethyl N-[4-(alkylamino)benzoyl]-L-glutamate with a C2-substituted 6-(bromo-methyl)-3

  强大的胸苷酸​​合酶（TS）抑制剂N- [4- [N-[（2-氨基-3,4-二氢-4-氧代-6-喹唑啉基）甲基] -N-丙-2-炔基氨基]苯甲酰基的修饰] -L-谷氨酸（1a）导致合成在C2带有烷基，取代的烷基和芳基取代基的喹唑啉抗叶酸酯。通常，合成路线包括将合适的N- [4-（烷基氨基）苯甲酰基] -L-谷氨酸二乙酯与C2-取代的6-（溴甲基）-3,4-二氢-4-氧喹唑啉偶联，然后进行偶联。用弱碱脱保护。发现在C2位置含有小的非极性基团的化合物具有良好的酶抑制作用和细胞毒性，其中2-desamino-2-methyl类似物3a最有效。该酶可耐受较大的C2取代基，但降低了细胞毒性。在合成一系列类似的N10取代基的类似物之后，进行了一系列有力的后续工作。以这种方式，已经制备了许多有趣的TS抑制剂。尽管这些化合物对分离的酶均没有比1a更有效的作用，但所制备的化合物中有一半以上对培养的L1210

表征谱图