DL-β-(5-Methylthiophen-2-yl)alanine | 154634-88-5

• 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: DL-β-(5-Methylthiophen-2-yl)alanine
• 英文别名: L-3-(5-methyl-thien-2-yl)alanine；beta-(5-Methylthiophen-2-yl)alanine；(2S)-2-amino-3-(5-methylthiophen-2-yl)propanoic acid
• CAS: 154634-88-5
• 化学式: C₈H₁₁NO₂S
• 分子量: 185.247
• InChiKey: KNSCRQAEJYEVMU-ZETCQYMHSA-N

物化性质

• 熔点：
  253-255 °C
• 沸点：
  324.9±42.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  DL-β-(5-Methylthiophen-2-yl)alanine 在 焦碳酸二乙酯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 (S)-2-[(S)-2-Amino-3-(5-methyl-thiophen-2-yl)-propionylamino]-3-(1H-imidazol-4-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Studies on cyclic dipeptides, I: Aryl modifications ofcyclo-[Phe-His]

  摘要：

  Seven new cyclic dipeptides have been synthesized and tested for their applicability as tools to elucidate the mechanism of formation of mandelonitrile with (SS)-cyclo-[Phe-His] type catalysts. Conformational analyses based on H-1 NMR spectra are presented for all prepared cyclic dipeptides.

  DOI：

  10.1007/bf00807581
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 在 盐酸 、 sodium hydroxide 、 L-天门冬氨酸 、 E_. coli strain 、 磷酸吡哆醛 、 水 、 sodium acetate 、 乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 DL-β-(5-Methylthiophen-2-yl)alanine
  参考文献：
  名称：

  Asymmetric synthesis of l-thienylalanines

  摘要：

  L-Thienylalanines were prepared via the hydantoin and azlactone routes with the key step consisting of the microbial transamination of 2-hydroxy-3-thienylacrylic with L-aspartic acid as amino donor. The transamination reaction was performed by a genetically engineered E. coli strain on scales up to 100 g of L-3-(2-thienyl)alanine 1a and is also applicable to the preparation of the isomeric amino acid 1b and some ring-substituted derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00016-5

文献信息

• METHODS OF TREATING SEROTONIN-MEDIATED DISEASES AND DISORDERS
  申请人：Brown Philip Manton

  公开号：US20090005381A1

  公开（公告）日：2009-01-01

  Methods are disclosed for treating serotonin-mediated diseases and disorders, which comprise inhibiting tryptophan hydroxylase (TPH) in patients in need thereof.

  本方法揭示了治疗由血清素介导的疾病和紊乱的方法，包括在需要的患者中抑制色氨酸羟化酶（TPH）。
• Treatment of immediate hypersensitivity diseases with aryl hydantoins
  申请人：Lilly Industries Limited

  公开号：US04241073A1

  公开（公告）日：1980-12-23

  Novel hydantoin compounds are described of the formula (I): ##STR1## wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C.sub.1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C.sub.1-4 alkoxy C.sub.1-4 alkyl, phenyl, hydroxyl, nitrile, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyloxy, C.sub.1-4 alkoxycarbonyl or phenoxy optionally substituted by C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen; or is thiophene optionally substituted by phenyl or by one or two C.sub.1-4 alkyl groups; R.sup.1 and R.sup.2 are independently hydrogen or taken together represent a chemical bond; R.sup.3 is hydrogen, C.sub.1-6 alkyl or C.sub.2-4 alkenyl; and R.sup.4 is C.sub.1-6 alkyl, C.sub.2-4 alkenyl, phenyl or benzyl; provided that R.sup.3 cannot be hydrogen when Ar is unsubstituted phenyl and R.sup.4 is n-butyl. The compounds are useful in the treatment of immediate hypersensitivity diseases including asthma.

  描述了一种新的咪唑啉化合物，其化学式为（I）：##STR1##其中Ar是苯基，可以选择性地取代为来自包括C.sub.1-6烷氧基、卤素、1,3-二氧杂环戊烷-2-基、羟基C.sub.1-4烷氧基C.sub.1-4烷基、苯基、羟基、腈基、C.sub.1-4卤代烷基、C.sub.1-4烷基、C.sub.2-4烯基氧基、C.sub.1-4烷氧羰基或苯氧基，可以选择性地取代为C.sub.1-4卤代烷基、C.sub.1-4烷氧基或卤素；或是噻吩，可以选择性地取代为苯基或一个或两个C.sub.1-4烷基基团；R.sup.1和R.sup.2独立地是氢原子或一起表示化学键；R.sup.3是氢原子，C.sub.1-6烷基或C.sub.2-4烯基；R.sup.4是C.sub.1-6烷基、C.sub.2-4烯基、苯基或苄基；但要求当Ar是未取代的苯基且R.sup.4是正丁基时，R.sup.3不能是氢原子。这些化合物在治疗包括哮喘在内的即时超敏症疾病中具有用途。
• Thenyl hydantoins and anti-asthmatic compositions thereof
  申请人：Lilly Industries Limited

  公开号：US04293563A1

  公开（公告）日：1981-10-06

  Novel hydantoin compounds are described of the formula (I): ##STR1## wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C.sub.1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C.sub.1-4 alkoxy C.sub.1-4 alkyl, phenyl, hydroxyl, nitrile, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyloxy, C.sub.1-4 alkoxycarbonyl or phenoxy optionally substituted by C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen; or is thiophene optionally substituted by phenyl or by one or two C.sub.1-4 alkyl groups; R.sup.1 and R.sup.2 are independently hydrogen or taken together represent a chemical bond; R.sup.3 is hydrogen, C.sub.1-6 alkyl or C.sub.2-4 alkenyl; and R.sup.4 is C.sub.1-6 alkyl, C.sub.2-4 alkenyl, phenyl or benzyl; provided that R.sup.3 cannot be hydrogen when Ar is unsubstituted phenyl and R.sup.4 is n-butyl. The compounds are useful in the treatment of immediate hypersensitivity diseases including asthma.

  本发明涉及一种新的脲嘧啶类化合物，其化学式为(I)：##STR1## 其中Ar是苯基，该苯基可选地被选自包括C.sub.1-6烷氧基，卤素，1,3-二氧杂环-2-基，羟基C.sub.1-4烷氧基C.sub.1-4烷基，苯基，羟基，腈基，C.sub.1-4卤代烷基，C.sub.1-4烷基，C.sub.2-4烯氧基，C.sub.1-4烷氧基羧基或选自C.sub.1-4卤代烷基，C.sub.1-4烷氧基或卤素取代的苯氧基取代的基团，或是噻吩基，该噻吩基可选地被苯基或一个或两个C.sub.1-4烷基取代；R.sup.1和R.sup.2分别是氢或一起表示化学键；R.sup.3是氢，C.sub.1-6烷基或C.sub.2-4烯基；R.sup.4是C.sub.1-6烷基，C.sub.2-4烯基，苯基或苄基；但是当Ar是未取代的苯基且R.sup.4是正丁基时，R.sup.3不能是氢。这些化合物可用于治疗包括哮喘在内的即时超敏反应性疾病。
• METHODS OF TREATING ULCERATIVE COLITIS
  申请人：Brown Philip Manton

  公开号：US20110263601A1

  公开（公告）日：2011-10-27

  Methods are disclosed for treating ulcerative colitis and related diseases and disorders, which comprise inhibiting tryptophan hydroxylase (TPH) in patients in need thereof.

  本文披露了治疗溃疡性结肠炎和相关疾病和疾病的方法，包括抑制需要此类治疗的患者中的色氨酸羟化酶（TPH）。
• METHODS FOR TREATING PULMONARY HYPERTENSION
  申请人：SANDS Arthur T.

  公开号：US20130274261A1

  公开（公告）日：2013-10-17

  Methods of treating pulmonary hypertension are disclosed. Particular methods comprise the administration of a tryptophan hydroxylase inhibitor and a prostacyclin. Pharmaceutical formulations are also disclosed.

  本发明公开了治疗肺动脉高压的方法。具体方法包括给予色氨酸羟化酶抑制剂和前列环素类的药物。同时还公开了相应的药物制剂。