methyl 2-benzyloxycarbonylamino-3-chloropropionate | 56618-03-2

• 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: methyl 2-benzyloxycarbonylamino-3-chloropropionate
• 英文别名: N^α-(Carbobenzyloxy)-β-chloroalanine methyl ester；N-benzyloxycarbonyl chloroalanine methyl ester；DL-N-(benzyloxycarbonyl)-3-chloroalanine methyl ester；methyl 2-(((benzyloxy)carbonyl)amino)-3-chloropropanoate；α-Benzyloxycarbonylamino-β-chlor-propionsaeure-methylester；L-methyl 2-benzyloxycarbonylamino-3-chloropropionate；Methyl 3-chloro-2-benzoxycarbonylaminopropionate；methyl 3-chloro-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 56618-03-2
• 化学式: C₁₂H₁₄ClNO₄
• 分子量: 271.7
• InChiKey: UQUQXYVMAKOZMV-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±45.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-benzyloxycarbonylamino-3-chloropropionate 在 sodium hydroxide 、 氯甲酸乙酯 、 sodium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 4.75h， 生成 Ethyl α-{(S)-2-benzyloxycarbonylamino-3-[4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine-1-yl]propionylamino}acetate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of some amino-acid-containing cyproheptadine derivatives as dual antagonists of histamine H1- and leukotriene D4-receptors

  摘要：

  A novel series of cyproheptadine derivatives, in which an amino acid or a dipeptide moiety was introduced at the piperidine nitrogen, have been synthesized. The amino acid and dipeptide moieties were taken as part of leukotriene D-4 (LTD(4)) pharmacophore. This modification reduced the H-1-antihistamine activity (100-1000-fold) but elevated the anti-LTD(4) activity (10-100-fold) of the compounds, as compared with cyproheptadine. As a result, some of the new compounds, especially the alpha-amino-propionic acid derivatives 4, are well-balanced dual antagonists of histamine and LTD(4) with both activities at micromolar range. Radioligand binding studies have confirmed that the new compounds, but not cyproheptadine for LTD(4), exert their action through competetive occupation of the receptors. One compound, (S)-2-benzyloxycarbonyl-amino-3-[4-(10,11-dihydro-5H-dibenzo [a,d]cyclo-hepten-5-yloxy)piperidin-1-yl]propionic acid (4c), was tested in an in vitro guinea-pig asthma model. It exhibits much more potent inhibition (IC50 = 1.5 mu M) against antigen-induced contraction than either terfenadine or FPL55712, the reference drugs. As indicated by an ex vivo binding assay, the drug 4c does not readily pass the blood-brain barrier, and therefore is unlikely to cause sedating side-effects at a therapeutic dose.

  DOI：

  10.1016/s0223-5234(97)87535-6
• 作为产物：
  描述：

  N-cbz-dl-丝氨酸甲酯 在 五氯化磷 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以58%的产率得到methyl 2-benzyloxycarbonylamino-3-chloropropionate
  参考文献：
  名称：

  乳酸菌素类似物的合成

  摘要：

  失活素（1）的氮杂类似物（一种最近发现的新型抗生素）是通过应用我们较早地方便合成1及其衍生物而制备的。带有2-氨基噻唑-4-基-（Z）-甲氧基亚氨基乙酰基的1-未取代的吡唑烷酮衍生物具有体外抗菌活性。

  DOI：

  10.1016/s0040-4020(01)85956-1

文献信息

• Piperidine derivatives
  申请人：Kowa Co., Ltd.

  公开号：US05714501A1

  公开（公告）日：1998-02-03

  A piperidine derivative of formula (1) or salts thereof: ##STR1## wherein R.sup.1 and R.sup.2 independently represent H or together represent O, R.sup.3 represents H, --R.sup.5 --COOR.sup.6, or --COOR.sup.6 (wherein R.sup.5 is a lower alkylene group, --CONH--, or --CONHCH.sub.2, and R.sup.6 is H or a lower alkyl group), R.sup.4 represents H, an aralkyloxy carbonyl group, an aminomethyl carbonyl group, or an aralkyloxy carbonyl aminomethyl carbonyl group, A represents O or a double bond, and the broken line has the meaning that a bonding hand may be present; and preventive and therapeutic agents for allergies, antihistaminic agents, and antileucotriene agents comprising the derivative or salts as their effective component. The compound of formula (1) has excellent antihistaminic activities and antileukotriene activities, which are well balanced, and is useful as a drug for the prevention and treatment of allergies such as asthma, allergic rhinitis, allergic dermatosis and urticaria.

  公式（1）的哒啶衍生物或其盐：##STR1##其中R.sup.1和R.sup.2独立地代表H或一起代表O，R.sup.3代表H，--R.sup.5--COOR.sup.6，或--COOR.sup.6（其中R.sup.5是较低的烷基烯基，--CONH--，或--CONHCH.sub.2，而R.sup.6是H或较低的烷基烯基），R.sup.4代表H，芳基氧羰基，氨甲基羰基，或芳基氧羰基氨甲基羰基，A代表O或双键，虚线表示键合手可能存在；以及包括该衍生物或其盐作为有效成分的过敏症预防和治疗剂，抗组胺剂和抗白三烯剂。公式（1）的化合物具有优异的抗组胺活性和抗白三烯活性，平衡性良好，并且可用作预防和治疗哮喘、过敏性鼻炎、过敏性皮肤病和荨麻疹等过敏症的药物。
• The Synthesis of Two Phenacetin Metabolites
  作者：A. Focella、P. Heslin、S. Teitel

  DOI：10.1139/v72-326

  日期：1972.7.1

  A new metabolite of phenacetin was identified as 4-hydroxy-3-methylthioacetanilide (11). The synthesis of 11 and the isomeric 4-hydroxy-2-methylthioacetanilide (4) as well as that of the previously reported phenacetin metabolite 3-[(5-acetamido-2-hydroxyphenyl)thio]alanine (18) is described.

  鉴定出苯乙酸对乙酰氨基酚的新代谢产物为4-羟基-3-甲基硫代苯胺（11）。描述了11和同分异构体4-羟基-2-甲基硫代苯胺（4）的合成，以及先前报道的苯乙酸代谢产物3-[(5-乙酰氨基-2-羟基苯基)硫基]丙氨酸（18）的合成。
• [EN] HETEROCYCLE DERIVATIVES FOR TREATING TRPM3 MEDIATED DISORDERS<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES POUR LE TRAITEMENT DE TROUBLES À MÉDIATION PAR TRPM3
  申请人：UNIV LEUVEN KATH

  公开号：WO2022112352A1

  公开（公告）日：2022-06-02

  The invention relates to compounds that are useful for the prevention or treatment of TRPM3 mediated disorders, more in particular disorders selected from pain and inflammatory hypersensitivity. The invention also relates to a method for the prevention or treatment of said TRPM3 mediated disorders.

  本发明涉及用于预防或治疗TRPM3介导的疾病的化合物，更具体地说是选自疼痛和炎症过敏的疾病。本发明还涉及一种预防或治疗所述TRPM3介导的疾病的方法。
• Cao, Yu; Christopherson, Richard I.; Elix, John A., Australian Journal of Chemistry, 1994, vol. 47, # 5, p. 903 - 912
  作者：Cao, Yu、Christopherson, Richard I.、Elix, John A.、Gaul, Kim L.

  DOI：——

  日期：——
• Chemistry of 2-substituted pyrimidines. Studies directed toward the synthesis of the pyrimidine moiety of bleomycin
  作者：William K. Hagmann、Fatima Z. Basha、Mitsunori Hashimoto、R. Bruce Frye、Shosuke Kojo、Sidney M. Hecht

  DOI：10.1021/jo00320a037

  日期：1981.3